Category: 885272-46-8

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. 885272-46-8, name is tert-Butyl 4-bromoindoline-1-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C13H16BrNO2

A mixture of the product of Step 1 (1.5 g, 5.0 mmol), allyltributylstannane (2.48 g, 7.5 mmol) and Pd(PPh3)4 (0.58 g, 0.5 mmol) in toluene (20 mL) was stirred at 100 C overnight under a nitrogen atmosphere. The mixture was loaded directly to a silica gel loading cartridge and purified by silica gel column chromatography with EtOAc in hexanes (0 to 10% gradient) to give the title compound (0.88 g, 68%). 1H NMR (CDC13) delta: 7.76 (br. s, 1H), 7.15 (t, J=7.7 Hz, 1H), 6.80 (d, J=7.6 Hz, 1H), 5.88- 5.98 (m, 1H), 5.01-5.11 (m, 2H), 3.93-4.09 (m, 2H), 3.32 (d, J=6.3 Hz, 2H), 3.04 (t, J=8.7 Hz, 2H), 1.57 (s, 9H).

The synthetic route of 885272-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; WANG, Jiashi; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; KARP, Gary, Mitchell; QI, Hongyan; WOLL, Matthew, G.; ZHANG, Nanjing; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Maria, L.; (260 pag.)WO2016/25933; (2016); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 885272-46-8, name is tert-Butyl 4-bromoindoline-1-carboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 885272-46-8

To a solution tert-butyl 4-bromoindoline-1-carboxylate (1.0 g, 3.354 mmol) and benzophenone hydrazone (0.658 g, 3.354 mmol) in 1,4-dioxane (15 mL) at room temperature under nitrogen, BINAP (209 mg, 0.335 mmol), palladium (II) acetate (75 mg, 0.335 mmol) and sodium t-butoxide (967 mg, 10.061 mmol) were added and the mixture was heated at 100 C. for 16 h. The resultant mixture was cooled to room temperature, filtered and the filtrate concentrated under reduced pressure to give the crude product, which was purified by flash chromatography (SiO2, heptane-ethyl acetate gradient). Pure fractions were combined and concentrated. The resultant solids were dried under reduce pressure to afford tert-butyl 4-(2-(diphenylmethylene)hydrazinyl)indoline-1-carboxylate, cpd 130a (912 mg, 65.8% yield). MS m/z 414.1 (M+H)+.

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:
Patent; Janssen Pharmaceutica NV; Lu, Tianbao; Connolly, Peter J.; Cummings, Maxwell David; Barbay, Joseph Kent; Kreutter, Kevin D.; Wu, Tongfei; Diels, Gaston Stanislas Marcella; Thuring, Jan Willem; Philippar, Ulrike; Edwards, James Patrick; Shen, Fang; (202 pag.)US2019/381019; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 885272-46-8, name is tert-Butyl 4-bromoindoline-1-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 885272-46-8

A solution of tert-butyl 4-bromoindoline-1-carboxylate (0.50g),bis(triphenylphosphine)palladium(II) dichioride (0.24 g), copper iodide (64 mg),triphenyiphosphine (0.18 g), hexamethyldisilazane (0.52 mL) and triethylamine (1.7 g) in DMF (8.4 mL) was evacuated and backfilied with nitrogen three times. The mixture was stirred for 10 minutes at 110 C. 2-[2-(4-Ethynylphenoxy)ethoxyjtetrahydropyran (0.83 g) was added into the mixture. The reaction mixture was stirred for 5 hours at 110 C and overnight at room temperature, quenched with water and extracted with EtOAc. The organiclayer was washed with water twice, dried over MgSO4, filtered and concentrated in vacuo. The residue was charged onto ISOLUTE HM-N and purified with OH-type silica gel column chromatography (3-100 % EtOAc in n-hexane) to give the title compound (0.57 g, 73 % yield) as a colorless solid.?H NMR (600 MHz, CHLOROFORM-d)6 ppm 1.50- 1.67(m, 13 H), 1.71 – 1.79(m, I H),1.81 – 1.89 (m, I H), 3.18 -3.25 (m, 2 H), 3.51 -3.57 (m,1H), 3.80-3.86 (m, I H), 3.87-3.93 (m, 1 H), 3.96 – 4.10 (m, 3 H), 4.13 – 4.23 (m, 2 H), 4.68 – 4.74 (m, 1 H), 6.89 – 6.94 (m,2 H), 7.05 – 7.17 (m, 2 H), 7.26 – 7.27 (m, 1 H), 7.40 – 7.48 (m, 2 H).

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:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; TAKASHIMA, Hajime; USHIYAMA, Fumihito; YAMADA, Yousuke; MATSUDA, Yohei; YOSHIZUMI, Takashi; KIM, Chunhae; YAMAGISHI, Junya; ARRATE, Alba Teresa Macias; ROUGHLEY, Stephen David; McKENNA, Sean; WALMSLEY, David Lee; (108 pag.)WO2018/216823; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem