4-Cyano-3-fluorophenyl 1-(triphenylmethyl)imidazol-4-yl ketone → 1-(4-Cyano-3-fluorophenyl)-1-[1-(triphenylmethyl)imidazol-4-yl]ethanol

To a solution of 4-cyano-3-fluorophenyl 1-(triphenylmethyl)imidazol-4-yl ketone, as described above in Step B, (7.0 g, 15.3 mmol) in dry THF (280 mL), under argon, at −78° C., was added MeMgBr (5.3 mL of a 3.0M solution in Et2O, 15.9 mmol), dropwise. After 1 hour, the reaction mixture was quenched with saturated aqueous NH4Cl (100 mL) and extracted with CH2Cl2 (2×150 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient of hexane—30% to 50% EtOAc, to yield the titled product as pale solid.

1. customthe reaction mixture was quenched with saturated aqueous NH4Cl (100 mL)
2. extractionextracted with CH2Cl2 (2×150 mL)
3. dry with materialThe combined organic extracts were dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue was purified by silica gel chromatography
7. washeluting with a gradient of hexane—30% to 50% EtOAc

ORD-Eintrag

ord-888fff0c422440cd97748750263c55c0

Quelldatensatz

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06441017B1