Sodium Chloride → methyl 1-benzyl-1H-indazole-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (0.37 g, 60%, 9.3 mmol) was added to a solution of indazole-3-carboxylic acid methyl ester (1.5 g, 8.5 mmol) in dry THF (50 mL) at 0° C. Benzyl bromide (1.59 g, 9.3 mmol) was then added and the reaction mixture was warmed to 25° C. and stirred for 8 h. The reaction mixture was poured onto saturated NaCl solution (100 mL) and extracted with 3×200 mL of diethyl ether. The combined extracts were dried (MgSO4) and concentrated under reduced pressure. The crude compound was purified by flash chromatography using cyclohexane/ethyl acetate (70:30) and recrystallised from cyclohexane/ethyl acetate to afford the title compound as a yellow solid (1.89 g,84%). Mp 72–73° C. 1H NMR (300 MHz, CDCl3) ppm 4.07 (s, 3H), 5.72 (s, 2H), 7.22–7.40 (m, 8H), 8.24–8.27 (m, 1H). MS(EI) m/z 266 [M+]. Anal. Calcd. for C16H14N2O2: C, 72.17; H, 5.30; N, 10.52. Found: C, 72.12; H, 5.15; N, 10.85.

Provenance & Evidence