Ethanone, 2,2,2-trifluoro-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)- synthesis

Yield:1032649-94-7 54%

Reaction Conditions:

with sodium hydride in N,N-dimethyl-formamide; for 0.5 h;

Steps:

8

Example 8: 3-{2,2,2-Trifluoro-l-[l-(4-fluorophenyl)-lH-indazol-5-yl]-l- hydroxyethyl}pyrrolo[2,3-6]pyridine-l-sulfonic acid dimethylamide; To a solution of 107 mg (0.5 mmol) of 2,2,2-trifluoro-l-(lH-pyrrolo[2,3-Z?]pyridin-3- yl)ethanone in 2 mL of DMF was added 60% sodium hydride in mineral oil followed by 80 mg (0.56 mmol) of N,N-dimethylsulfamoyl chloride. The mixture stirred for 30 minutes and was then diluted with 10 mL of saturated aqueous sodium bicarbonate and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with three 7 mL portions of brine, three 7 mL portions of saturated aqueous ammonium chloride, dried over magnesium sulfate, filtered and concentrated. The crude material was adsorbed onto silica gel and chromatographed on silica gel eluting with ethyl acetate-hexanes (10-100% gradient) to afford 88 mg (54%) of 3-(2,2,2-trifluoroacetyl)pyrrolo[2,3-Z?]pyridine-l -sulfonic acid dimethylamide as a white solid.

References:

WO2008/70507,2008,A2 Location in patent:Page/Page column 118