Tetrahydrofuran → HCID 59152923, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of {(R)-4-[(3-bromo-5-trifluoromethyl-benzenesulfonyl)-methyl-amino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid ethyl ester (example 2-5) (prepared by the method analogous to the one described for example 2-1) (290 mg, 0.556 mmol) and a solution of cyclopentylzinc bromide in tetrahydrofuran (0.5 M, 10.0 mL, 5.0 mmol), bis(dibenzylideneacetone)palladium(0) (16.7 mg, 0.028 mmol) and tris(tert-butyl)phosphine (178 μL, 0.056 mmol) were added under an argon atmosphere. After being stirred at 50° C. for 1 hour, the mixture was concentrated in vacuo. Saturated ammonium chloride was added and the mixture was extracted with ethyl acetate (20 mL×3). The organic layers were combined, washed with saturated ammonium chloride, dried over sodium sulfate and concentrated in vacuo to afford {(R)-4-[(3-cyclopentyl-5-trifluoromethyl-benzene-sulfonyl)-methyl-amino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid ethyl ester (220 mg, 77%) as a viscous oil which was used for the next step without any purification. MS cald. for C24H30F3N3O4S 513, obsd. (ESI+) [(M+H)+] 514.

Provenance & Evidence