Dichloromethane → HCID 52913223, compound

Participants

Reaction Steps

A solution of the product of Example 41, step A (86 mg, 0.21 mmol) in dichloromethane (2.5 mL) at 0° C. was treated with boron tribromide (2.5 mL, 2.1 mmol). The reaction was stirred for 4 h then quenched with methanol followed by saturated sodium bicarbonate. The mixture was extracted with dichloromethane and the organic extract concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 95:5 dichloromethane/methanol) and the residue dissolved in a minimum of methanol. The solution was treated with 1.25 M HCl in methanol (2 mL) then concentrated in vacuo to give 2-(3-hydroxyphenyl)sulfonyl-5-methyl-5,6,7,8,9,10-hexahydro-7,10-epiminocyclohepta[b]indole hydrochloride (21 mg, 23%, AUC HPLC >99%) as an off-white solid: mp 208-212° C.; 1H NMR (DMSO-d6, 300 MHz) δ 10.20 (s, 1H), 8.90-9.40 (m, 2H), 8.32 (s, 1H), 7.60-7.67 (m, 2H), 7.29-7.39 (m, 2H), 7.25 (s, 1H), 6.98 (s, 1H), 5.32-5.39 (br s, 1H), 4.46 (br s, 1H), 3.70 (s, 3H), 3.37-3.39 (m, 1H), 3.01 (d, J=17.0 Hz, 1H), 2.26 (br s, 2H), 2.06-2.12 (m, 1H), 1.72-1.86 (m, 1H). ESI MS m/z 369 [M+H]+

Provenance & Evidence