Boron Trichloride → HCID 118062201, compound

Participants

Reaction Steps

To a stirred solution of Intermediate 260A (70 mg, 0.137 mmol) in DCM (10 mL), cooled to −78° C., was added BCl3 (0.547 ml, 0.547 mmol, 1.0 M in DCM) and the resulting mixture was allowed to warm to RT and stir for 16 h. The reaction mixture was quenched with a saturated aqueous solution of NH4Cl and extracted with DCM (3×25 mL). The combined organic layers were dried over Na2SO4 and evaporated. The crude compound was purified by preparative HPLC to afford Compound 260 as an off-white solid (9.0 mg, 16% yield). HPLC Ret. Times 6.51 min. and 6.54 min. (HPLC Methods A and B). MS(ES): m/z=422 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.86 (dd, J=7.31, 2.16 Hz, 1H), 7.69 (dt, J=6.24, 2.49 Hz, 1H), 7.43-7.48 (t, 1H), 7.11-7.41 (m, 2H), 6.96 (s, 1H), 6.68 (s, 1H), 4.90 (dd, J=10.42, 6.15 Hz, 1H), 4.70 (s, 2H), 4.08-4.18 (m, 2H), 3.97 (m, 1H), 3.82 (s, 2H), 2.45-2.56 (m, 1H), 2.26-2.38 (m, 1H), 1.95-1.98 (m, 1H), 1.70-1.75 (m, 1H), 1.74 (s, 1.5H), 1.24-1.40 (s, 1.5H).

Provenance & Evidence