Imidazole → HCID 87214270, compound

Participants

Reaction Steps

Iodination of alcohol 187 with I2, PPh3 and imidazole as in Example 2GGG above for 18 h, followed by chromatography of the product on silica gel, eluting with petroleum ether and pentane (foreruns) and then with 5-25% Et2O/pentane, gave 2-bromo-5-[3-{[tert-butyl(dimethyl)silyl]oxy}-2-(iodomethyl)propoxy]pyridine (188) (97%) as a colourless oil; 1H NMR (CDCl3) δ 8.07 (d, J=3.0 Hz, 1H), 7.37 (dd, J=8.7, 0.3 Hz, 1H), 7.11 (dd, J=8.7, 3.2 Hz, 1H), 4.06 (dd, J=9.2, 5.7 Hz, 1H), 3.99 (dd, J=9.2, 6.1 Hz, 1H), 3.74 (dd, J=10.1, 5.6 Hz, 1H), 3.70 (dd, J=10.1, 5.5 Hz, 1H), 3.36 (d, J=6.0 Hz, 2H), 2.12 (sept, J=5.8 Hz, 1H), 0.89 (s, 9H), 0.06 (2 s, 6H); HRESIMS calcd for C15H26BrINO2Si m/z [M+H]+ 487.9935, 485.9955. found 487.9931, 485.9952.

Provenance & Evidence