Methyl iodide → HCID 66896785, compound

Temperature

-20 °C

A solution of diisopropyl amine (0.51 mL, 3.6 mmol) in tetrahydrofuran (12 mL) at −20° C., was treated with n-butyl lithium (2.5 M in hexanes, 1.45 mL, 3.6 mmol) and the solution was stirred for 10 minutes. A solution of Preparation 80 (4-(1-(4-methoxyphenyl)-1H-imidazol-5-yl)pyridine, 730 mg, 2.9 mmol) in tetrahydrofuran was added and the solution became dark orange. The solution was stirred for 30 minutes as the temperature was allowed to rise to 0° C. After cooling to −20° C., methyl iodide (0.54 mL, 8.7 mmol) in tetrahydrofuran (12 mL) was added and the solution was stirred for 30 min at −20° C. and for 2 hr at 23° C. The solvent was removed in vacuo, the residue was diluted with brine and was extracted with ethyl acetate. The organic layer was then dried (MgSO4), was filtered, and was concentrated in vacuo. The residue was purified by silica gel chromatography using ethyl acetate-hexanes-methanol (63:32:5 to 72:18:10) to afford 555 mg (72% yield) of the title compound; diagnostic 13C NMR signals (100 MHz, CDCl3) δ 160.144, 150.034, 149.197, 137.749, 131.265, 129.463, 128.985, 128.828, 120.849, 115.233, 55.78, 14.203; MS (AP/Cl) 266.4 (M+H)+.

1. additionwas added
2. stirringThe solution was stirred for 30 minutes as the temperature
3. customto rise to 0° C
4. stirringthe solution was stirred for 30 min at −20° C. and for 2 hr at 23° C
5. customThe solvent was removed in vacuo
6. additionthe residue was diluted with brine
7. extractionwas extracted with ethyl acetate
8. dry with materialThe organic layer was then dried (MgSO4)
9. filtrationwas filtered
10. concentrationwas concentrated in vacuo
11. customThe residue was purified by silica gel chromatography

ORD record

ord-2ef1ac219f814db7b0fa3649d68f75be

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07429665B2