Methanol → HCID 69642180, compound

Participants

Reaction Steps

Oxalyl chloride (1.8 mL, 20.7 mmol) was added dropwise to a solution of 7-bromoindole (3.65 g, 18.6 mmol) in Et2O (100 mL) cooled in an ice bath. After the addition was complete, the ice bath was removed and the mixture was allowed to warm to room temperature and stirred for 8 h. The mixture was then cooled in a dry ice-acetone bath and a 25% by wt solution of sodium methoxide in methanol (9.5 mL, 41.8 mmol) added dropwise over 5 min. The suspension was allowed to warm to room temperature affording a yellow suspension. After stirring 1 h at rt, the suspension was treated with water and the mixture poured into EtOAc. The EtOAc solution was separated and washed with pH 7.0 buffer and brine, dried (MgSO4) and concentrated to ˜75 mL. The solution was diluted with Et2O and allowed to stand. Filtration afforded the title compound as pale yellow crystals (0.61 g, 12%). Concentration of the mother liquor to a slurry followed by addition of a small amount of Et2O (20 mL) and filtration afforded a second crop (2.33 g, 44%). 1H NMR (400 MHz, DMSO-d6) 12.68 (br s, 1H), 8.46 (br s, 1H), 8.17 (d, J=8 Hz, 1H), 7.54 (d, J=8 Hz, 1H), 7.23 (dd, J=8, 8 Hz, 1H), 3.90 (s, 3H). 13C NMR (75.5 MHz, DMSO-d6) 178.63, 163.34, 138.72, 135.06, 127.16, 126.45, 124.27, 120.51, 113.22, 105.03, 52.59. IR (CHCl3, cm−1) 3450, 1731, 1654. MS (electrospray, m/z) 284/282 (M++1), 282/280 (M−−1). HRMS 281.9786 (M++1, calcd for C11H9NO3Br 281.9766). Anal. Calcd for C11H8BrNO3: C, 46.84; H, 2.86; N, 4.97. Found: C, 46.81; H, 2.72; N, 4.91.

Provenance & Evidence