Lithium diisopropylamide → (4-(2-bromophenyl)-1-trityl-1H-imidazol-2-yl)(3-(tert-butyldimethylsilyloxy)-5-ethyl-2-fluorophenyl)methanol

Temperatur

0 °C

To a solution of Intermediate 217.1 (650 mg, 1.40 mmol) in 10 mL THF at 0° C., was added a solution of lithium diisopropylamide (2M in heptane/THF/ethylbenzene, 0838 mL, 1.68 mmol). The mixture was stirred at 0° C. for 30 min, then a solution of Intermediate 188.3 (356 mg, 1.26 mmol) in 2 mL THF. The mixture was stirred at 0° C. for 2 h, then was quenched with sat. NH4Cl and diluted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient) to afford 510 mg of Intermediate 217.2 as a pale yellow solid. LCMS (50 to 100% B, 4 min gradient, A=95% H2O/5% CH3CN/0.1% TFA, B=5% H2O/95% CH3CN/0.1% TFA) RT=5.61 min, 747.67 (M+H)+.

1. stirringThe mixture was stirred at 0° C. for 2 h
2. customwas quenched with sat. NH4Cl
3. additiondiluted with EtOAc
4. washThe organic phase was washed with H2O and brine
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customThe crude product was purified by flash chromatography (0 to 40% EtOAc/hexanes gradient)

ORD-Eintrag

ord-acad0d528b6945de8eb0136a07900e16

Quelldatensatz

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07576098B2