Imidazole → HCID 58573628, compound

To a 0° C. solution of iodine (1.094 g, 4.31 mmol) and imidazole (0.294 g, 4.31 mmol) in dichloromethane (10.27 ml) was added portionwise triphenylphosphine (1.131 g, 4.31 mmol). After 20 min of stirring, (6-methoxypyridin-2-yl)methanol (Adesis, New Castle, Del., 0.5 g, 3.59 mmol) was added to the solution. The reaction was allowed to stir for 1 h at 0° C., quenched with water (50 mL) and extracted with Et2O. The combined organics were dried over MgSO4, and concentrated in vacuo. Silica gel chromatography (gradient elution 1 to 5% Et2O in pentane) afforded 2-(iodomethyl)-6-methoxypyridine. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.49 (dd, J=7.3, 8.3 Hz, 1H), 6.96 (d, J=7.1 Hz, 1H), 6.61 (d, J=8.1 Hz, 1H), 4.44 (s, 2H), 3.94 (s, 3H). Mass Spectrum (ESI) m/z=249.9 (M+1).

1. stirringto stir for 1 h at 0° C.
2. customquenched with water (50 mL)
3. extractionextracted with Et2O
4. dry with materialThe combined organics were dried over MgSO4
5. concentrationconcentrated in vacuo
6. washSilica gel chromatography (gradient elution 1 to 5% Et2O in pentane)

ORD record

ord-816d9c697c804e94a25fc57a6c419ffc

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296736B2