Boron tribromide → HCID 66939497, compound

Participants

Reaction Steps

To a cooled (0° C.) solution of the title compound from Example 17 Step A (353 mg, 0.888 mmol) in DCM (6.3 ml) was added BBr3 (2.67 ml, 1.0 M in DCM, 2.67 mmol) dropwise. After the addition was complete, the mixture was allowed to warm up to ambient temperature. After 1 h, the reaction mixture was quenched by addition of sat. aq. NaHCO3 and extracted with DCM. The organic phase was separated and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 60% EtOAc in hexanes) provided the title compound as a yellow solid: LCMS m/z 384.5 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 10.17 (s, 1H), 8.18 (s, 1H), 7.67 (dd, J=8.0, 1.9 Hz, 1H), 7.34 (t, J=8.5 Hz, 1H), 7.09 (dd, J=8.2, 0.9 Hz, 1H), 6.98 (t, J=7.4 Hz, 1H), 4.45 (m, 2H), 1.44 (t, J=7.1 Hz, 3H).

Provenance & Evidence