Sodium Carbonate → (5-(9-bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-2-yl)-1-isopropyl-1H-1,2,4-triazol-3-yl)methanol

Participants

Reaction Steps

A solution of 8-bromo-2-(2-isopropyl-5-methoxymethyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene 309 (280 mg, 0.67 mmol) in 48% aqueous HBr (4.19 mL) was heated at 100° C. for 4 h before cooling to RT. The solution was neutralized by the addition of 1M aqueous sodium carbonate and then extracted with DCM, the organic layer washed with water then dried (Na2SO4), filtered and concentrated in vacuo to give [5-(8-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-2-yl)-1-isopropyl-1H-[1,2,4]triazol-3-yl]-methanol as a cream solid (162 mg, 60%). LCMS RT=4.74 min, [M+H]+=404. 1H NMR 400 MHz (DMSO-d) δ: 8.30 (1 H, d, J=8.65 Hz), 7.91 (1 H, s), 7.33 (1 H, dd, J=8.65, 2.06 Hz), 7.27 (1 H, d, J=2.03 Hz), 5.82-5.75 (1 H, m), 5.18 (1 H, t, J=6.03 Hz), 4.51 (4 H, s), 4.40 (2 H, d, J=5.99 Hz), 1.44 (6 H, d, J=6.60 Hz)

Provenance & Evidence