Hydrochloric Acid → HCID 59152879, compound

Participants

Reaction Conditions

Reaction Steps

To a solution 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) (1.0 g, 1.9 mmol) in N,N-dimethylformamide (8 mL) was added tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (175 mg, 0.19 mmol), triphenylarsine (Ph3As) (175 mg, 5.72 mmol) and 1-ethoxy-vinyltributyltin (1 mL, 2.86 mmol). After being stirred at 80° C. for 2 hours under an argon atmosphere, the reaction mixture was cooled to room temperature, 4N hydrochloric acid (1 mL) was added, and the mixture was stirred at room temperature for 20 minutes. The resulting mixture was poured into water (40 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with water (20 mL) and brine (20 mL), and then concentrated in vacuo. The residue was purified by flash column (gradient elution: 15-30% ethyl acetate in petroleum ether) to afford {(R)-4-[(3-acetyl-5-trifluoromethyl-benzenesulfonyl)-methyl-amino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid ethyl ester as a yellow oil (800 mg, 86.4%). MS cald. for C21H24F3N3O5S 487, obsd. (ESI+) [(M+H)+] 488.

Provenance & Evidence