Category: 13861-75-1

Adding a certain compound to certain chemical reactions, such as: 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 13861-75-1, Application In Synthesis of Spiro[cyclopropane-1,3′-indolin]-2′-one

Bromine (0.15 mL, 3.0 mmol) was added drop-wise to a mixture of spiro[cyclopropane-1,3′-[3H]indol]-2′(1’H)-one (486 mg, 3.05 mmol), 174 muL (3.0 mmol) acetic acid (0.174 mL, 3.0 mmol) and sodium acetate (250 mg, 3.0 mmol) in dry dichloromethane (120 mL). After 4 h, the reaction was washed with 5% sodium thiosulfalte and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 5′-bromospiro[cyclopropane-1,3′-indol]-2′(1’H)-one (0.75 g, 100%) as a white solid. This compound was used without further purification.

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Reference:
Patent; Wyeth; US2006/30615; (2006); A1;,
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Synthetic Route of 13861-75-1, These common heterocyclic compound, 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[0272] To a cooled (0C) solution of spiro[cyclopropane-l,3′-indolin]-2′-one (prepared according to methods described in J. Med. Chem. 1987, 824-829; J. Med. Chem. 1992, 163-172; U.S. Patent 5,182,397) (1.0 g, 6.21 mmol) in NN-dimethylformamide (5 mL), was added sodium hydride (0.149 g, 6.21 mmol), followed by addition of l-bromo-3-chloropropane (0.733 mL, 7.45 mmol, d = 1.6). After stirring at room temperature for 18 hours, the reaction mixture was diluted with ethyl acetate (100 mL), washed with dilute citric acid, water and brine. The organic phase was dried over MgS04, filtered and isolated by Biotage flash chromatography (10-40% ethyl acetate/hexanes) to obtain the title compound (1.1 g, 68%); ¾ NMR (DMSO-i 6): delta 1.50-1.54 (m, 2H), 1.56-1.61 (m, 2H), 2.01- 2.15 (m, 2H), 3.67 (t, 2H, J= 6.4 Hz), 3.86 (t, 2H, J= 6.8 Hz), 6.97-7.03 (m, 2H), 7.11 (d, 1H, J= 8 Hz), 7.22-7.27 (m, 1H); MS for Ci3H14ClNOm/z 236.04 (M+H)+.

The synthetic route of 13861-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALTOS THERAPEUTICS, LLC; LUEHR, Gary, W.; SUNDARAM, Arathi; JAISHANKAR, Priyadarshini; PAYNE, Philip, W.; DRUZGALA, Pascal; WO2011/160084; (2011); A1;,
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Related Products of 13861-75-1, The chemical industry reduces the impact on the environment during synthesis 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, I believe this compound will play a more active role in future production and life.

EXAMPLE 5 N-(1-azabicyclo[2.2.2]octan-4-ylmethyl)-2′-oxo-spiro[cyclopropane-1,3′-[3’H]indole]-1′(2’H)-carboxamide, monohydrochloride STR13 To sodium hydride (92 mg, 2.31 mmol) (washed 2* with hexane) suspended in THF (1 ml) was added spiro[cyclopropane-1,3′-[3’H]indol]-2′(1’H)-one (92 mg, 0.578 mmol) and the reaction was stirred for 5 minutes. The resulting suspension was added to a solution of 20% phosgene in toluene (2.29 ml, 4.62 mmol) in THF (2 mL) and stirred for 0.5 hour. The reaction mixture was then filtered through celite and concentrated in vacuo to give a beige solid which was dissolved in THF (5 ml) and treated with a solution of 4-aminomethyl quinuclidine (81 mg, 0.578 mmol) as prepared in Example A in THF (2 ml) and stirred for 18 hours. Concentration in vacuo gave a solid which was dissolved in chloroform, washed with 1N NaOH solution, dried over K2 CO3, filtered and concentrated in vacuo to give the crude desired compound as a solid. Purification on silica gel eluding with 10% CH3 OH(NH3)/CHCl3 gave the title compound (35 mg, 19%). The free base (59 mg, 0.181 mmole) was converted to the hydrochloride salt by treatment with methanolic HCl to give the monohydrochloride (57 mg, 91%) as a solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Spiro[cyclopropane-1,3′-indolin]-2′-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; G. D. Searle & Co.; US5399562; (1995); A;,
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Electric Literature of 13861-75-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1,2-dihydro-3-spiro-1′-cyclopropyl-1H-indole-2-one (2.5 g crude) in THF (50 mL) was added LiAlH4 (2 g, 52 mmol) portionwise. After heating the mixture to reflux, it was poured into crushed ice, basified with aqueous ammonia to pH 8 and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give the crude 1,2-dihydro-3-spiro-1′-cyclopropyl-1H-indole as a yellow solid (about 2 g), which was used directly in the next step.

The synthetic route of Spiro[cyclopropane-1,3′-indolin]-2′-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 13861-75-1, Recommanded Product: 13861-75-1

A. Preparation of 5′-(1-oxopropyl)spiro-[cyclopropane-1,3′-[3H]indol]-2′(1’H)-one A slurry was made from 7.5 ml of dimethylformamide and 45.5 g of anhydrous aluminum chloride. The temperature rose to 40 C. and 2.97 ml of propionyl chloride and 5.43 g of spiro[cyclopropane-1,3′-[3H]-indol]-2′(1’H)-one were added. The mixture was stirred for 2 hours at 70 C. and was slowly poured into a mixture of ice and 50 ml of concentrated hydrochloric acid. After cooling overnight, the resulting precipitate was recovered by filtration. Crystallization from ethyl acetate provided 4.9 grams of the desired subtitle intermediate, m.p. 183-185 C. Analysis for C13 H13 NO2: Calculated: C, 72.54; H, 6.09; N, 6.51; Found: C, 72.47; H, 6.14; N, 6.42.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Eli Lilly and Company; US4617302; (1986); A;,
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Synthetic Route of 13861-75-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The spiro [cyclopropane-1,3′-indol] -2′-one 63a (3g, 18.8mmol) was dissolved in 3mL of acetonitrile at room temperature was added 2-bromo-1,1-dimethoxyethane ( 3.34g, 19.7mmol), potassium carbonate (12.25g, 37.6mmol), potassium iodide (10mg), the reaction was stirred for 16 hours at room temperature. The reaction solution was concentrated under reduced pressure, the reaction solution was added 100mL of water, extracted with ethyl acetate (100mL × 2), and the combined organic phase was washed with water (100mL × 3), washed with saturated sodium chloride solution (100mL × 2), dried over anhydrous dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. By column chromatography (PE: EtOAc = 4: 1) to give purified 1 ‘- (2,2-dimethoxy-ethyl) spiro [cyclopropane-1,3′-indol] -2′-one 63b (2g, yellow solid), yield: 43.0%.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Spiro[cyclopropane-1,3′-indolin]-2’-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Mingde New Drug Research And Development Co. Ltd; HE, HAI-YING; SHI, WEI-HUA; JIANG, ZHI-GAN; HAN, LI-XIA; SUN, JI-KUI; LI, JIAN; CHEN, SHU-HUI; (175 pag.)TW2016/5834; (2016); A;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, A new synthetic method of this compound is introduced below., Formula: C10H9NO

A 5 mL microwave vial equipped with a stirrer bar was charged with spiro[cyclopropane-1,3?-indolin]-2?-one (20 mg, 0.125 mmol, 1 equiv) and MgI2 (1.74 mg, 6.25 mumol, 5 mol%) before being capped and purged with N2. THF (0.6 M, 0.2 mL) and trimethyl triazinane (18 muL, 0.125 mmol, 1 equiv) were then added and the reaction mixture was heated to 125 C in a sand-bath for 60 h. The reaction mixture was then cooled to r.t. before being diluted with EtOAc (5 mL) and washed with H2O (5 mL) and brine (5 mL). The organic layers were then passed through a hydrophobic frit and concentrated under vacuum before being purified (silica gel; EtOAc-petroleum ether, 50% then MeOH-CH2Cl2, 20%) to afford the desired product. Yield: 14 mg (55%); pale-yellow oil. IR (solid): 3192, 3060, 2943, 2787, 1707, 1619, 1472, 1336, 1195 cm-1. 1H NMR (400 MHz, CDCl3): delta = 8.45 (s, 1 H), 7.41 (d, J = 7.3 Hz, 1 H), 7.19 (td, J = 7.7, 1.2 Hz, 1 H), 7.04 (td, J = 7.6, 1.0 Hz, 1 H), 6.89 (d, J =7.7 Hz, 1 H), 3.11-3.00 (m, 1 H), 2.91 (s, 2 H), 2.88-2.74 (m, 1 H), 2.49 (s, 3 H), 2.41 (ddd, J = 12.5, 7.7, 4.7 Hz, 1 H), 2.12 (dt, J = 12.9, 7.5 Hz,1 H). 13C NMR (101 MHz, CDCl3): delta = 182.7, 140.1, 136.0, 127.8, 123.4, 122.9, 109.5, 66.2, 56.7, 53.6, 41.8, 38.0. HRMS (NSI): m/z [M + H]+ calcd for C12H15N2O: 203.1179; found: 203.1177.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Seath, Ciaran P.; Fyfe, James W. B.; Molloy, John J.; Watson, Allan J. B.; Synthesis; vol. 49; 4; (2017); p. 891 – 898;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, A new synthetic method of this compound is introduced below., SDS of cas: 13861-75-1

1-4 (6.0 g, 37.7 mmol) was dissolved in chloroform (480 mL), and PIFA (19.5 g, 45.2 mmol) and trifluoroacetic acid (43 g, 376.9 mmol, 28 mL) were added. The reaction mixture was stirred at 25 C for 12 hours. The reaction mixture was neutralized with a saturated sodium carbonate solution to pH = 7-8, extracted with dichloromethane/methanol (100 mL × 3), and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was washed with petroleum ether/ethyl acetate (100 mL × 2), and filtered to give the target compound 1-5. 1H NMR (400MHz, CHLOROFORM-d) delta 6.68 – 6.70 (d, J = 8.0 Hz 1H), 6.55 – 6.58 (m, 2H), 6.26 – 6.27 (d, J = 2.0 Hz 1H), 1.59- 1.62 (m, 2H), 1.38 – 1.41 (m, 2H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Application of 13861-75-1, A common heterocyclic compound, 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, molecular formula is C10H9NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 2: Spiro [cycJ.opropane-1, 3 ?-indoline]To mixture of spiro[cyclopropane-l, 3?-indoiine]-2?-one(35.0 g, 219.87 mmol) in THF? (750 mL) was slowly added lithiumaluminium hydride (2M solution in THF) (219.9 mL, 439.7 mrnol) at 0C. The resulting mixture was allowed to be warmed to room temperature and then heated to reflux for 18 hour under argon atmosphere. Upon completion as monitored by TLC, the reactionmixture was cooled to room temperature, quenched with ice, basified with aqueous ammonia, and extracted with ethyl acetate (2 x 750 mL) . The combined organic layers were washed. successively with water (100 rn) and brine (100 mL), dried over sodium sulfate and concentrated under vacuum to obtain acrude oily product (32 g, 100%) . The product was subjected tonext reaction without further purification.MS(ESI)m/z: 146.1[M+1] ; ?HNMR (400 MHz, DMSO-d6) : 5 0.88 (s, 4H)3.43 (S. 21-{), 5.54 (s, 1H), 6.44-6.55 (m, 3H), 6.85 (t, J =7.6 Hz, 1M).

The synthetic route of 13861-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; DESHPANDE, Anil M.; BARAWKAR, Dinesh; PATIL, Santosh; BANKAR, Digambar; (178 pag.)WO2016/88903; (2016); A1;,
Indoline – Wikipedia,
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13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C10H9NO

Example 3 1′-((1-isopentyl-1H-benzo[d]imidazol-2-yl)methyl)spiro[cyclopropane-1,3′-indolin]-2′-one A dried flask under nitrogen was charged with sodium hydride (120 mg, 3.0 mmol) and DMF (1 mL). This rapidly stirred suspension was cooled to 0 C. using an ice/water bath and spiro[cyclopropane-1,3′-indolin]-2′-one (160 mg, 1.0 mmol, Preparatory Example 4) was added dropwise as a solution in DMF (2 mL). The ice/water bath was removed for 15 minutes before the mixture was recooled to 0 C. and 2-(chloromethyl)-1-isopentyl-1H-benzo[d]imidazole hydrochloride (236 mg, 1.0 mmol) was added dropwise as a solution in DMF (2.1 mL). The mixture was allowed to warm to rt and stirred there for 16 hours. The mixture was cooled to 0 C. and ice was added carefully. Partition between EtOAc and water was followed by separation, drying and concentration in vacuo. Preparative HPLC gave isolation of the desired compound, (110 mg, 0.31 mmol, 31%). 1H NMR (400 MHz): delta 0.96 (d, 6H), 1.45 (m, 2H), 1.60 (m, 2H), 1.69 (m, 1H), 1.82 (m, 2H), 4.26 (m, 2H), 5.35 (s, 2H), 6.83 (d, 1H), 7.02 (dd, 1H), 7.19 (dd, 1H), 7.29 (m, 3H), 7.47 (d, 1H), 7.81 (m, 1H). LC/MS 360 (MH+).

The synthetic route of 13861-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; re: Viral Ltd; Cockerill, Stuart; Pilkington, Christopher; Lumley, James; Angell, Richard; Mathews, Neil; US2014/308282; (2014); A1;,
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