Water → 2-(4-{[4-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbonyl]-amino}-3-cyclohex-1-enyl-phenyl)-2-methyl-propionic acid methyl ester

Temperatur

80 °C

A mixture of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-bromo-2-cyclohex-1-enyl-phenyl)-amide (as prepared in Example 1, step (f), 100 mg, 0.200 mmol), (1-methoxy-2-methyl-propenyloxy)-trimethyl-silane (61 μL, 0.30 mmol), Pd(t-Bu3P)2 (10.2 mg, 0.0200 mmol) and ZnF2 (10.3 mg, 0.100 mmol) in 2 mL of DMF was stirred at 80° C. for 2 d under Ar. After cooling to RT, the mixture was treated with H2O (20 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with H2O (10 mL) and brine (10 mL). After drying over Na2SO4 and concentrating in vacuo, the residue was purified by silica gel chromatography (DCM) to afford the title compound (48 mg, 46%) as a colorless oil. LC-MS (ESI, m/z): Calcd. for C28H38N4O4Si, 523.3 (M+H). found 523.0.

1. temperatureAfter cooling to RT
2. extractionextracted with EtOAc (2×20 mL)
3. washThe combined organic layers were washed with H2O (10 mL) and brine (10 mL)
4. dry with materialAfter drying over Na2SO4
5. concentrationconcentrating in vacuo
6. customthe residue was purified by silica gel chromatography (DCM)

ORD-Eintrag

ord-c72c4f939e5f4d0898a199718082a11a

Quelldatensatz

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09221797B2