Tetrahydrofuran → 3-Bromo-5-(1-ethenylcyclopropyl)pyridine

Participants

Reaction Steps

To a solution of methyltriphenylphosphonium bromide-sodium amide complex (510 mg, 01.22 mmol) in tetrahydrofuran (2.0 mL) was added a solution of the title compound from Example 73 Step B (97 mg, 0.43 mmol) in tetrahydrofuran (1.0 mL) The reaction stirred at room temperature for 16 hours. It was then quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The organic extracts were combined, washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-100% ethyl acetate in hexanes) provided the title compound: LCMS m/z 225.77 [M+H]+; 1H NMR (500 MHz, CD3OD) δ 8.54 (s, 1H), 8.47 (s, 1H), 7.50 (s, 1H), 5.68 (dd, J=10.4, 17.1, 1 H), 4.98 (d, J=10.4, 1 H), 4.62 (d, J=17.1, 1 H), 1.12-1.05 (m, 4H).

Provenance & Evidence