Pyridine → HCID 22347011, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (0.07 mL, 0.79 mmol) was added into a solution of indole-3-carboxylic acid (0.12 g, 0.72 mmol) in dichloromethane (4 mL) and tetrahydrofuran (3 mL) at 0° C. N,N-dimethylforamide (3 drops from 0.1 mL syringe) was added and the mixture was stirred at 0° C. for 10 minutes and at ambient temperature for 20 minutes. The solvents and excess of reagents were evaporated under reduced pressure. The residue was taken into dichloromethane (2 mL) and the resulting solution (1.5 mL) was added into a solution of 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.09 g, 0.36 mmol) and pyridine (1 mL) in dichloromethane (2 mL). The mixture was stirred at ambient temperature overnight. The acid chloride solution in dichloromethane (0.3 mL) was added in and the mixture was stirred overnight. Water (a drop) was added in. The volatile components were evaporated under reduced pressure. The residue was partitioned between water and ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate. The organic extracts were combined and washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The mixture was filtered and the solvent of the filtrate was evaporated to yield the crude which was purified by flash column chromatography on silica using n-heptane:ethyl acetate (2/1) as a mobile phase to yield N3-[2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1H-3-indolecarboxamide (0.11 g, 0.28 mmol) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 8.65 (m, 3H), 8.13 (d, 1H), 7.95 (s, 1H), 7.50 (m, 2H), 7.33(m, 3H), 4.02 (s, 3H), 1.36 (s, 12H); MS: MH+ 393.

Provenance & Evidence