Imidazole → HCID 21099382, compound

HRID 2376984Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2F)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[NH:33]1[CH:37]=[CH:36][N:35]=[CH:34]1>CS(C)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:33]2[CH:37]=[CH:36][N:35]=[CH:34]2)(=[O:18])=[O:19])=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 150 °C

Procedure

2,4-Difluoro-1-(2-{4-[(2-fluorophenyl)sulfonyl]phenyl}ethyl)benzene (Example 124, 100 mg, 0.26 mmol), potassium carbonate (126 mg, 0.39 mmol) and imidazole (26 mg, 0.39 mmol) were combined in dimethylsulfoxide (1.3 mL) and heated in a microwave reactor at 150° C. for 20 minutes. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 5% ethanol/ethyl acetate to yield the title compound as a white solid (85 mg, 77%). δH (400 MHz, d6 DMSO): 8.31-8.29 (1H, m), 7.87-7.79 (2H, m), 7.41-7.39 (2H, m), 7.31-7.23 (5H, m), 7.16-7.12 (1H, m), 6.99-6.95 (1H, m), 6.88 (1H, t, J=1.1 Hz), 6.85 (1H, t, J=1.3 Hz), 2.92-2.84 (4H, m). m/z (ES+) 425 [MH+].

Workup

washwashed with water and brine
dry with materialdried over Na2SO4
customevaporated in vacuo
customThe residue was purified by flash column chromatography on silica
washeluting with 5% ethanol/ethyl acetate

Sources & evidence

ORD record: ord-d6f52c4662894a4787f6e222ff6cacf5
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468393B2

Reaction notes

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