Sulfuric Acid → HCID 67775937, compound

Participants

Reaction Steps

To a solution of an approximately 1:1 mixture of compound (v) and compound (vi) (14.2 mg, 0.032 mmol) in 1,4-dioxane (5 mL) and water (5 mL) was added sodium borohydride (28 mg, 0.74 mmol) and the reaction was stirred at RT for 1 h. The reaction mixture was acidified with 2 N aqueous sulfuric acid, then diluted with water (15 mL) and extracted with EtOAc (2×30 mL). The combined organic extracts were washed with brine (7 mL), dried (MgSO4) and evaporated to dryness. The residue was purified by flash column chromatography eluting with EtOAc/heptane (50-100%) to give racemic 5-cyclopropyl-6-[3-hydroxy-1-(methylsulfonyl)propyl]-N-methyl-2-(4-methylphenyl)-2H-indazole-3-carboxamide (viii) as a white solid (11 mg, 79%).

Provenance & Evidence