Sodium triacetoxyborohydride → HCID 178523757, compound

Participants

Reaction Steps

To a solution of Cis-2-Chloro-N-(4-formyl-cyclohexyl)-5-trifluoromethyl-benzamide (100 mg, 0.300 mmol) in DCM (3 mL) is added 3-(4-fluorophenyl)-1H-pyrazol-5-amine (58.4 mg, 0.330 mmol) to give a pale orange solution. This is stirred for 10 mins at room temperature before sodium triacetoxyborohydride (102 mg, 0.479 mmol) is added. The reaction mixture is stirred at room temperature for 1 hour. The reaction mixture is quenched by the addition of saturated sodium bicarbonate. The DCM layer is separated and further washed with water. The aqueous extracts are combined and re-extracted with DCM. The combined organic extracts are then dried over MgSO4, filtered and concentrated under vacuum. Purification by chromatography on a pre-packed 12 g silica gel column using 0-100% EtOAc in isohexane (gradient elution) gave the desired product as a colourless solid. [MH+495.29].

Provenance & Evidence