反应详情

163 mg (0.323 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, 13 mg (0.016 mmol) of dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct, and 100 mg (0.356 mmol) of 2-amino-3-fluoro-5-iodo-benzoic acid were placed in a microwave vial. To the vial were added 2 mL of acetonitrile and 2 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 90° C. for 300 seconds. The resulting mixture was diluted with ethyl acetate and washed with water. The aqueous layer was back extracted three times with ethyl acetate. The combined organic phases were 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 135 mg (0.254 mmol, 78% yield) of 2-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid as a brown residue. MS: m/z 532.0 (M+H+).

1. customThe vial was sealed
2. custompurged with nitrogen
3. customevacuated with vacuum (3×)
4. customThe vial was irradiated in a microwave at 90° C. for 300 seconds
5. additionThe resulting mixture was diluted with ethyl acetate
6. washwashed with water
7. extractionThe aqueous layer was back extracted three times with ethyl acetate
8. dry with materialThe combined organic phases were dried over sodium sulfate
9. customevaporated
10. customThe resulting residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate and hexanes
11. concentrationThe clean fractions were concentrated