Reference of 337536-15-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 337536-15-9, name is 4-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows.
Example 10 4-{5-[3-chloro-5-(trifluoromethoxy)phenyl]-1-(pyridine-3-yl)-1H-pyrazole-3-yl}-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-1-one Step 4 [0572] In four parallel procedures, four portions of 175 mg (0.42 mmol) of the product from step 3 are each dissolved in 5 ml dioxane and combined with 128 mg (0.50 mmol) of bis-pinakolato-diboron, 123 mg (1.26 mmol) potassium acetate and 21 mg (0.025 mmol) [1,1-bis-(diphenyl-phosphino)ferrocene]-dichloropalladium-dichloro-methane complex. Each reaction mixture is stirred in the microwave for 1 h at 120 C., cooled to RT, combined with 85 mg (0.50 mmol) of the compound from example 22A, 0.42 ml (2 N in water, 0.84 mmol) of a sodium carbonate solution and 17 mg (0.02 mmol) [1,1-bis-(diphenylphosphino)ferrocene]-dichloropalladium-dichloromethane complex and stirred for 2 h at 120 C. The reaction mixtures are combined. The suspension is diluted with acetonitrile, filtered through a Millipore filter and separated by preparative HPLC (solvent: acetonitrile/water gradient). Once the resulting solid has crystallized out of the acetonitrile, this produces 286 mg (36% of theoretical yield) of the title compound. Example 11 4-{5-[3-chloro-5-(trifluoromethoxy)phenyl]-1-(pyridine-3-yl)-1H-pyrazole-3-yl}-2,3-dihydro-1H-isoindole-1-one [0575] [0576] The synthesis of the title compound is performed starting from 100 mg (0.24 mmol) of the product from step 3 of the compound from example 10 in a manner analogous to step 4 of the synthesis of the compound from example 10. Instead of the compound from example 22A, 4-bromo-2,3-dihydroisoindole-1-on (61 mg, 0.29 mmol) is used. This produces 28 mg (24% of theoretical yield, 94% purity) of the title compound. [0577] 1H-NMR (400 MHz, DMSO-d6): delta=4.73 (s, 2H), 7.21 (s, 1H), 7.51-7.60 (m, 2H), 7.61-7.69 (m, 3H), 7.72 (d, 1H), 7.89 (d, 1H), 8.17 (d, 1H), 8.61-8.71 (m, 2H), 8.75 (s, 1H). [0578] LC-MS (Method 3): Rt=1.13 min; MS (ESIpos): m/z=471 [M+H]+.
The chemical industry reduces the impact on the environment during synthesis 4-Bromoisoindolin-1-one. I believe this compound will play a more active role in future production and life.
Reference:
Patent; AICURIS GMBH & CO. KG; Wildum, Steffen; Klenke, Burkhard; Wendt, Astrid; US2015/203500; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem