Some common heterocyclic compound, 337536-15-9, name is 4-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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. category: indolines-derivatives
Example 6 4-{5-[3-fluoro-5-(trifluoromethoxy)phenyl]-1-(pyridine-3-yl)-1H-pyrazole-3-yl}-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-1-one Step 4 [0553] In three parallel mixtures, each of three 100 mg (0.25 mmol) portions of the product from step 3 is dissolved in 5 ml dioxane in each case and each is combined with 76 mg (0.30 mmol) of bis-pinakolato-diboron, 73 mg (0.75 mmol) potassium acetate and 12 mg (0.017 mmol) [1,1-bis-(diphenyl-phosphino)ferrocene]-dichloropalladium dichloromethane complex. The reaction mixtures are stirred for 1 h in the microwave at 120 C. and cooled to RT, then combined with 50 mg (0.30 mmol) of the compound from example 22A, 250 mul (2 N in water, 0.50 mmol) sodium carbonate solution and 10 mg (0.013 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 in a small amount of 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 174 mg (51% of theoretical yield) of the title compound. Example 7 4-{5-[3-fluoro-5-(trifluoromethoxy)phenyl]-1-(pyridine-3-yl)-1H-pyrazole-3-yl}-2,3-dihydro-1H-isoindole-1-one [0556] title compound is performed starting from 100 mg (0.25 mmol) of the product from step 3 of the compound from example 6 in a manner analogous to step 4 from example 6, whereby instead of the compound from example 22A, 4-bromo-2,3-dihydroisoindole-1-on (63 mg, 0.30 mmol) is used. This produces 64 mg (56% of theoretical yield) of the title compound. [0558] 1H-NMR (400 MHz, DMSO-d6): delta=4.73 (s, 2H), 7.12 (s, 1H), 7.43 (dt, 1H), 7.48-7.58 (m, 3H), 7.64 (t, 1H), 7.72 (d, 1H), 7.85-7.91 (m, 1H), 8.16 (d, 1H), 8.64 (d, 1H), 8.67 (d, 1H), 8.75 (s, 1H). [0559] LC-MS (Method 3): Rt=1.07 min; MS (ESIpos): m/z=455 [M+H]+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 337536-15-9, its application will become more common.
Reference:
Patent; AICURIS GMBH & CO. KG; Wildum, Steffen; Klenke, Burkhard; Wendt, Astrid; US2015/203500; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem