HCID 22941953, compound → HCID 22941957, compound

Participants

Reaction Steps

A stirred solution of 3-(6-[3-pyrrolidin-1-yl-1-{4-tolyl}-prop-1E-enyl]-pyridin-2-yl)-prop-2E-enal (1.41 g, 4.24 mmol) in anhydrous THF (50 ml) at -78° C. was treated dropwise with a solution of methyl magnesium bromide (1.56 ml, 3.0M in diethylether, 4.67 mmol). The reaction mixture was allowed to warm slowly to room temperature (~2 hours). The reaction was quenched with water (3 ml) and THF removed under reduced pressure. The residue was taken up in 1M HCl and then basified with solid sodium bicarbonate to pH 8. The product was extracted with ethyl acetate (×3). The organics were combined, dried over sodium sulphate, filtered and concentrated under reduced pressure. The product was purified by column chromatography eluting with 5% methanol in DCM. Product containing fractions were combined and solvent removed to provide 4-(6-[3-pyrrolidin-1-yl-1-{4-tolyl}-prop-1E-enyl]-pyridin-2-yl)-but-3E-en-2-ol as a pale brown foam (544 mg, 37%). 1H-NMR; δ (CDCl3), 7.43 (1H, t, J=7.8 Hz), 7.24-7.18 (3H, m), 7.11-7.06 (3H, m), 6.94 (1H, dd, J=15.6 and 5.8 Hz), 6.71-6.64 (2H, m), 4.60-4.55 (1H, m), 3.23 (2H, d, J=7.0 Hz), 2.58 (4H, bs), 2.41 (3H, s), 1.82-1.77 (4H, m), 1.41 (3H, d, J=6.5 Hz).

Provenance & Evidence