Acetic Acid → HCID 49869632, compound

Participants

Reaction Steps

AcOH (0.42 mL) and picoline borane complex (51 mg, 0.47 mmol) were added to 4-((5-fluoropyridin-2-yl)methoxy)-1-(1,2,3,4,5,6-hexahydroazepino[4,5-b]indol-8-yl)-pyridin-2(1H)-one (69 mg, 0.16 mmol) suspended in 1:1 CH2Cl2/acetone (4.8 mL), and the resulting suspension was heated at reflux for 68 h. Additional acetone (1.0 mL) and picoline borane complex (20 mg, 19 mmol) were added, and the resulting suspension heated at reflux for 68 h. The reaction was cooled and concentrated to dryness under reduced pressure. 1 N HCl (10 ml) was added, and the suspension stirred at ambient temperature for 2 h. The mixture was made basic with 1 N NaOH and extracted with CH2Cl2 (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. Preparative TLC (Analtech, 20×20 cm, 1000 microns, 80:18:2 CH2Cl2/MeOH/NH4OH) provided the title compound (31 mg, 43%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.86 (s, 1H), 8.61 (d, J=2.5 Hz, 1H), 7.82-7.81 (m, 1H), 7.66-7.63 (m, 1H), 7.55 (d, J=8.0 Hz, 1H), 7.40 (d, J=8.5 Hz, 1H), 7.14 (s, 1H), 6.82 (d, J=7.0 Hz, 1H), 6.09 (dd, J=7.5, 3.0 Hz, 1H), 5.95 (d, J=3.0 Hz, 1H), 5.20 (s, 2H), 3.02-2.98 (m, 1H), 2.86-2.85 (m, 2H), 2.76 (m, 6H), 1.02 (d, J=6.5 Hz, 6H); ESI MS m/z 447 [M+H]+.

Provenance & Evidence