HCID 59547946, compound → HCID 59547991, compound

Participants

Reaction Steps

To a solution of 4-[(3-{[(2,6-difluorophenyl)carbonyl]amino}-1H-pyrazol-1-yl)methyl]-3-(trifluoromethyl)benzoic acid (for a preparation see Intermediate 21)(0.340 g, 0.80 mmol) in THF (5 ml) at ambient temperature under nitrogen was added 1.0 M borane-tetrahydrofuran complex (1.3 ml, 1.30 mmol). The solution was stirred at ambient temperature under nitrogen for 1 h. To the suspension was added a further amount of 1.0 M borane-tetrahydrofuran complex (1.3 ml, 1.30 mmol). The solution was stirred for a further 2 h. The solvent was removed in vacuo to leave a colourless gum. The residue was re-dissolved in THF (5 ml). To the solution was added 1.0M boran-tetrahydrofuran complex (2 ml, 2 mmol) and stirred for 6 h. The solution was quenched with methanol (10 ml), stirred for 5 min and then the solvent removed in vacuo. The residue was loaded in dichloromethane and purified on silica (20 g) using 0-100% ethyl acetate-cyclohexane+0-20% methanol. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a colourless gum (0.20 g);

Provenance & Evidence