Water → HCID 11632832, compound

HRID 2067946Notes

Reaction equation

Cl[C:2]([C:13]1[N:14]=[C:15]([CH3:31])[N:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=2)[C:17]=1[CH3:18])=[C:3]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]([Cl:12])[CH:7]=1)C=O.CC(C)([O-])C.[K+].O>C1COCC1>[Cl:12][C:8]1[CH:7]=[C:6]([C:3]#[C:2][C:13]2[N:14]=[C:15]([CH3:31])[N:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([C:27]([F:30])([F:28])[F:29])[CH:20]=3)[C:17]=2[CH3:18])[CH:11]=[CH:10][N:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-Chloro-2-(2-chloro-pyridin-4-yl)-3-[1-(4-methoxy-3-trifluoromethyl-phenyl)-2,5-dimethyl-1H-imidazol-4-yl]-propenal (0.9 g, 1.9 mmol) in 8 mL THF was dropped to a cold (0° C.) suspension of potassium tert-butoxide (0.47 g, 4.2 mmol) in 4 mL THF and water (0.04 mL, 2.1 mmol). The light brown reaction mixture was stirred at 0° C. for 1 hr. The reaction was extracted two times with ethyl acetate, saturated NaHCO3− solution, water and brine. The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The crude product was purified by chromatography on silica gel (n-heptane/ethyl acetate 90:10→0:100) to obtain the desired product as a white solid (0.15 g, 19%), MS: m/e=406.2 (M+H+).

Workup

extractionThe reaction was extracted two times with ethyl acetate, saturated NaHCO3− solution, water and brine
dry with materialThe combined organic extracts were dried with sodium sulfate
filtrationfiltered
customevaporated
customThe crude product was purified by chromatography on silica gel (n-heptane/ethyl acetate 90:10→0:100)

Sources & evidence

ORD record: ord-b7250b070b824433983294d4add27433
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293916B2

Reaction notes

Loading…