Methyl iodide → 3-Bromo-4-(1-methoxy-ethyl)-pyridine

Reaction equation

[H-].[Na+].[Br:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[CH:10]([OH:12])[CH3:11].I[CH3:14]>CN(C=O)C>[Br:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[CH:10]([O:12][CH3:14])[CH3:11]

Participants

Procedure

Sodium hydride (60% in mineral oil, 148 mg, 3.71 mmol) was added to a solution of 1-(3-bromopyridin-4-yl)ethanol (500 mg, 2.475 mmol) in DMF (12 mL) at 0° C. After 10 min, iodomethane (1.237 mL, 2.475 mmol) was added dropwise and the resulting mixture was stirred at room temperature for another 1 h. The reaction was quenched by water, and the mixture was extracted with ethyl acetate. The combined extracts were dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by flash column (ethyl acetate-heptane, v/v, 0-30%) to give 418 mg of the title compound. 1HNMR (CDCl3, 400.3 MHz) δ 1.42 (d, J=6.4 Hz, 3H), 3.30 (s, 3H), 4.64 (q. J=0.4 Hz, 1H), 7.58 (s, 1H), 8.56 (s, 1H), 8.70 9s, 1H).