Dihydro-3(2H)-thiophenone → 3-(5-(5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)thiazol-2-yl)tetrahydrothiophen-3-ol

Participants

Reaction Conditions

Reaction Steps

A solution of Example 144A (0.095 g, 0.202 mmol) in tetrahydrofuran (2.5 mL) was cooled to −78° C. and treated with n-butyllithium (2.45 M in hexanes, 0.173 mL, 0.424 mmol) dropwise over 5 minutes. The reaction was stirred at −78° C. for 20 minutes, and dihydrothiophen-3(2H)-one (0.033 mL, 0.384 mmol) was added. The reaction was stirred 60 minutes at −78° C. and was quenched by addition of saturated aqueous sodium bicarbonate solution. The mixture was allowed to warm to ambient temperature and was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by flash chromatography on a silica gel column, eluting with 1% methanol in dichloromethane, to provide the title compound. MS ESI(+) m/z 572.3 [M+H]+.

Provenance & Evidence