Hexane → 5-bromo-3-[1-(2,6-dichloro-3-fluorophenyl)-2-fluoro-2,2-bis(phenylsulfonyl)ethyl]-1H-pyrrolo[2,3-b]pyridine

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Reaction Conditions

Reaction Steps

To a stirred solution of 1-(fluoro(phenylsulfonyl)methylsulfonyl)benzene (836 mg, 2.66 mmol) in THF (8.0 mL) was added 2.5 M of n-BuLi in Hexane (1.18 mL, 2.95 mmol) at −78° C.; the resulting mixture was stirred for 30 min at −78° C. before use. To a stirred solution of (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2,6-dichloro-3-fluorophenyl)methanol (250.0 mg, 0.6410 mmol) in THF (5.0 mL, 62 mmol) was added thionyl chloride (0.12 mL, 1.6 mmol) at 0° C. The resulting mixture was stirred for 30 min at rt, then the solvent was removed and the residue was dried under high vacuum. To this residue was added THF (10.0 mL) followed by adding the previously prepared solution (lithiated 1-(fluoro(phenylsulfonyl)methylsulfonyl)benzene) by canula at −78° C. The resulting mixture was allowed to warm up to rt in about 1 hr. Then the solvent was removed under reduced pressure to give a residue, which was diluted by DCM and extracted by DCM (20 mL×3). The organic phase were combined, dried (Na2SO4) and concentrated to give a crude residue, which was purified by silica gel chromatography (eluent: 20% AcOEt in DCM) to give the title compound. MS (ES+): m/z 684.92, 686.92, 688.92 [MH+]. HPLC: tR=1.65 min (polar—3 min, TOF)

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