Boron tribromide → HCID 59161229, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve N-[6-chloro-9-(2-methoxy-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (Example 19) (100 mg, 0.24 mmol) in anhydrous dichloromethane (3 mL) under nitrogen and cool in a brine/ice bath to 0° C. Slowly add boron tribromide (1M in dichloromethane, 1.22 mL, 1.22 mmol). After 30 min remove the ice bath and allow to warm to ambient temperature over 4 h. Dilute with ethyl acetate (12 mL) and wash with water. Extract aqueous portion with ethyl acetate (3×). Combine all organic portions, wash with water, brine, dry (MgSO4), and concentrate in vacuo to obtain a residue. Elute the residue over a silica pad with 25% ethyl acetate/dichloromethane to obtain 93 mg (96%) of a tan solid. MS (ES): m/z 397, 399 (M+1), 395, 397 (M−1); 1H NMR(DMSO-d6): δ 9.83 (s, 1H), 7.85 (d, 1H, J=7.9 Hz), 7.45 (s, 1H), 7.33 (d, 1H, J=8.4 Hz), 7.04 (m, 2H), 6.86 (d, 1H, J=7.9 Hz), 6.63 (t, 1H, J=7.3 Hz), 6.32 (d, 1H, J=7.5 Hz), 5.23 (s, 2H), 4.02 (m, 1H), 2.95 (dd, 1H, J=15.2, 5.1 Hz), 2.84-2.66 (m, 2H), 2.52 (m, 1H), 2.40 (m, 1H), 1.97 (m, 1H), 1.80 (m, 1H), 1.02 (m, 7H).

Provenance & Evidence