Sodium Hydroxide → HCID 66873343, compound

Participants

Reaction Steps

NaOH (0.44 g, 11 mmol) was added to a solution of tert-butyl 8-(4-benzyloxy)-2-oxopyridin-1(2H)-yl)-6-tosyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (0.14 g, 0.22 mmol) in 1:1 CH2Cl2/MeOH (20 mL), and the resulting solution was heated at reflux for 18 h. The mixture was diluted with H2O and was extracted with CH2Cl2 (3×20 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to dryness. Flash chromatography (12 g ISCO column, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 5 column volumes, increased to 25:75 over 20 column volumes and held for 2 column volumes) provided the title compound (58 mg, 55%) as a yellow film: 1H NMR (500 MHz, DMSO-d6) δ 11.08-11.05 (m, 1H), 7.54 (d, J=8.0 Hz, 1H), 7.48-7.35 (m, 6H), 7.19 (s, 1H), 6.87 (d, J=8.0 Hz, 1H), 6.06 (dd, J=7.0, 2.0 Hz, 1H), 5.95 (d, J=2.5 Hz, 1H), 5.14 (s, 2H), 4.55 (s, 2H), 3.65 (t, J=5.0 Hz, 2H), 2.94 (t, J=5.5 Hz, 2H), 1.83-1.80 (m, 2H), 1.35-1.28 (m, 9H).

Provenance & Evidence