Sodium Bicarbonate → 2-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide

Participants

Reaction Steps

548 mg (1.09 mmol) of 3-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine, 89 mg (0.109 mmol) of dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct and 368 mg (1.19 mmol) of 2-amino-3-fluoro-5-iodo-N,N-dimethyl-benzamide were placed in a microwave vial. To the vial were added 6 mL of acetonitrile and 5 mL of a saturated aqueous solution of sodium bicarbonate. The vial was sealed and purged with nitrogen and evacuated with vacuum (3×). The vial was irradiated in a microwave at 80° C. for 500 seconds. The resulting mixture was diluted with ethyl acetate and washed with water and brine. The layers were separated and the organic layer was dried over sodium sulfate and evaporated. The resulting residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexanes. The clean fractions were concentrated to afford 490 mg (0.877 mmol, 81% yield) of 2-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide as a peach foam. MS: m/z 559.2 (M+H+).

Provenance & Evidence