Boron tribromide → HCID 178422184, compound

Participants

Reaction Steps

To a heterogeneous mixture of 4-(3-(6-chloro-1-oxoisoindolin-2-yl)-2-methylphenyl)-7-methoxy-9H-pyrido[3,4-b]indole-1-carboxamide (prepared in the same manner as Example 15) (0.277 g, 0.557 mmol) in dichloromethane (20 mL) at 0° C. was added tribromoborane in dichloromethane (2.79 mL, 2.79 mmol) over 5 min. The heterogeneous mixture was stirred at room temperature for 3 hr and then poured into ice cold water (20 mL). The resulting mixture was basified with saturated NaHCO3 solution to pH 8 and extracted with ethyl acetate (3×40 mL). The combined extract was washed with brine (30 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (0.217 g, 85% purity, 0.382 mmol, 68.5% yield) as a yellow solid. A pure sample was obtained through prep. reverse phase HPLC purification. LCMS (M+H)+=483.15. 1H NMR (500 MHz, DMSO-d6) δ: 11.61 (s, 1H), 9.89 (s, 1H), 8.34 (s, 1H), 8.20 (s, 1H), 7.88 (s, 1H), 7.81-7.77 (m, 3H), 7.72 (dd, J1=7.8 Hz, J2=1.2 Hz, 1H), 7.58 (m, 1H), 7.48 (dd, J1=7.5 Hz, J2=1.2 Hz, 1H), 7.23 (d, J=2.0 Hz, 1H), 7.12 (d, J=8.6 Hz, 1H), 6.60 (dd, J1=8.7 Hz, J2=2.3 Hz, 1H), 5.10 (d, J=17.6 Hz, 1H), 4.99 (d, J=17.6 Hz, 1H), 1.92 (s, 3H).

Provenance & Evidence