Boron tribromide → HCID 54766104, compound

Participants

Reaction Steps

Boron tribromide (0.16 mL, 1M in CH2Cl2, 0.16 mmol) was added dropwise to a solution of 1-(2-(4-(5-methoxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-inden-1-yl)phenoxy)ethyl)pyrrolidine (18 mg, 0.04 mmol) and dichloromethane (2.5 mL) at 0° C. under N2. After 20 min, the reaction was allowed to warm to rt. After an additional hour, the reaction was quenched with methanol (0.4 mL), poured into saturated aqueous NaHCO3 (40 mL), and extracted with 5% methanol in dichloromethane (50 mL×2). The organic extracts were dried (MgSO4), filtered, concentrated, and purified by reverse-phase HPLC (CH3CN, H2O, TFA) to give 10 mg of 2-(4-hydroxyphenyl)-1-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-2,3-dihydro-1H-inden-5-ol as the trifluoroacetate salt. 1H NMR (400 MHz, DMSO-d6): δ 9.61 (br, 1H), 9.22 (br, 1H), 8.99 (br, 1H), 6.81-6.75 (m, 2H), 6.72-6.62 (m, 4H), 6.60-6.52 (m, 3H), 6.44 (d, 2H), 4.45 (d, 1H), 4.15 (t, 2H), 3.91-3.79 (m, 1H), 3.62-3.48 (m, 4H), 3.23-2.98 (m, 4H), 2.08-1.80 (m, 4H); LCMS: 416.6 (M+H)+.

Provenance & Evidence