Acetic Acid → 1-[2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazol-4-yl]-1-ethanone

HRID 1353012Notes

Reaction equation

C[Li].[Li+].[Br-].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]([C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[CH:14]=[C:15]([C:17](N(OC)C)=[O:18])[N:16]=2)=[CH:8][CH:7]=1.C[Li].[C:35](O)(=O)C>O1CCCC1>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:13]([C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:30])=[O:31])=[CH:25][CH:24]=3)[CH:14]=[C:15]([C:17](=[O:18])[CH3:35])[N:16]=2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl lithium-LiBr complex (1.5 M in ethyl ether) (0.47 ml, 0.7 mmol) was added by syringe to a cold (−70° C.) solution of 2-(4-chlorophenyl)-N-methoxy-N-methyl-1-[4-(methylsulfonyl)phenyl]-1H-imidazole-4-carboxamide from step 2 (250 mg, 0.6 mmol) in 50 ml tetrahydrofuran. The reaction was warmed to 0° C. and re-cooled to −60° C. before additional methyl lithium (0.47 ml) was added. The reaction was warmed to room temperature. After stirring for two days, 50 ml of 10% acetic acid was added and the mixture was concentrated to a gum. The gum was dissolved in 50 ml ethyl acetate, washed with water (2×50 ml), dried over Na2SO4, filtered and concentrated. The product was purified by silica gel chromatography: Anal. Calc'd. C18H15N2O3SCl.¼H2O: C, 56.99; H, 4.12; N, 7.38. Found: C, 56.88; H, 4.05; N, 7.6838

Workup

additionwas added
temperatureThe reaction was warmed to room temperature
concentrationthe mixture was concentrated to a gum
dissolutionThe gum was dissolved in 50 ml ethyl acetate
washwashed with water (2×50 ml)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-6eaaf9e295644f3b90d15b7ce40feedd
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220770B2

Reaction notes

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