Bromine → HCID 11462335, compound

Participants

Reaction Steps

The product of Example 24F (150 mg, 0.5 mmol) was treated with KSCN (Aldrich, 97 mg, 1 mmol) and bromine (Aldrich, 96 mg, 0.6 mmol) in HOAc (5 mL) at ambient temperature for 0.5 h. It was then quenched with Na2SO3 (aq. 10%, 1 mL) and concentrated. The title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:2, Rf. 0.1) as solid (170 mg, yield, 80%). 1H NMR (300 MHz, CD3OD) δ 1.60-1.70 (m, 1H), 1.72-1.98 (m, 2H), 2.02-2.19 (m, 1H), 2.23-2.42 (m, 1H), 2.82-3.13 (m, 5H), 3.42-3.68 (m, 1H), 5.15-5.54 (m, 1H), 7.26 (d, J=9.2 Hz, 1H), 7.49 (d, J=8.5 Hz, 1H), 7.87 (dd, J=8.6, 1.9 Hz, 1H), 8.07 (d, J=9.5 Hz, 1H), 8.23 (d, J=1.4 Hz, 1H) ppm. MS (DCI/NH3): 354 (M+H)+.

Provenance & Evidence