Sodium Ascorbate → HCID 86635703, compound

Participants

Reaction Steps

A mixture of 5-azido-1H-indazole (126 mg, 789 μmol), (R)-tert-butyl 1-(6-(trifluoromethyl)pyridin-3-yl)hex-5-yn-2-ylcarbamate (270 mg, 789 μmol), CuSO4 (6.3 mg, 39 μmol), and sodium ascorbate (16 mg, 79 μmol) in t-BuOH/H2O (1:1, 2 mL) was stirred at room temperature for 8 hours. The mixture was partitioned between saturated aqueous NaCO3 (15 mL) and DCM (15 ml). The layers were separated and the aqueous layer was extracted with CH2Cl2 (2×15 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting yellow solid was dissolved in MeOH/DCM, absorbed onto silica gel, and purified by flash chromatography (silica gel, 3% to 8% MeOH/DCM) to deliver tert-butyl(R)-4-(1-(1H-indazol-5-yl)-1H-1,2,3-triazol-4-yl)-1-(6-(trifluoromethyl)pyridin-3-yl)butan-2-ylcarbamate (85 mg, 21%) as a light yellow solid. LCMS (API-ES) m/z: 502.1 (M+H+).

Provenance & Evidence