Dimethylamine → 2-(4-Benzyloxy-5-fluoro-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

Participants

Reaction Steps

A solution of oxalyl chloride (0.78 mL, 8.963 mmol) in anhydrous ether (20 mL) was added dropwise over 20 min to a 0° C. solution of 1-5a (1.44 g, 5.975 mmol) in anhydrous ether (20 mL). The reaction mixture was stirred at room temperature for 5 h, cooled to −20° C., and treated with a stream of dimethyl amine gas. The reaction was diluted with EtOAc, washed with water and brine, and dried over Na2SO4. After concentration, the resulting residue was recrystallized from EtOAc to provide the product (1-6a) as white crystals in 87% yield, 1.58 g. 1H NMR (300 MHz, CDCl3-d) δ (ppm) 2.92 (s, 3H), 2.94 (s, 3H), 5.17 (s, 2H), 6.91-7.00 (m, 2H), 7.29-7.37 (m, 3H), 7.58-7.61 (m, 2H), 7.70-7.72 (m, 1H), 10.02 (br, 1H). APCI [M+1]: 341.2.

Provenance & Evidence