N-bromobutanimide → HCID 178520386, compound

HRID 216401Notes

Reaction equation

HRID 216401 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][CH:10]([F:38])[C:11]([C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH:37]=[CH:36][CH:35]=[N:34]2)=[CH:29][CH:28]=1)([OH:26])[CH2:12][C:13]1[NH:14][CH:15]=[C:16]([CH2:18][C:19]2([C:22]([F:25])([F:24])[F:23])[CH2:21][CH2:20]2)[N:17]=1>C(#N)C>[Br:1][C:15]1[NH:14][C:13]([CH2:12][C:11]([C:27]2[CH:28]=[CH:29][C:30]([N:33]3[CH:37]=[CH:36][CH:35]=[N:34]3)=[CH:31][CH:32]=2)([OH:26])[CH:10]([F:9])[F:38])=[N:17][C:16]=1[CH2:18][C:19]1([C:22]([F:25])([F:24])[F:23])[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178520387HCID 178520387, compound

Product 1

HCID 178520386HCID 178520386, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Bromosuccinimide (95 mg, 0.53 mmol) was added to a solution of 1,1-difluoro-2-[4-(1H-pyrazol-1-yl)phenyl]-3-(4-{[1-(trifluoromethyl)cyclopropyl]methyl}-1H-imidazol-2-yl)propan-2-ol (200 mg, 0.53 mmol) in acetonitrile (5 mL) at ambient temperature. After stirring for 1 hr, the reaction mixture was concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl acetate/hexane afforded 3-(5-bromo-4-{[1-(trifluoromethyl)cyclopropyl]methyl}-1H-imidazol-2-yl)-1,1-difluoro-2-[4-(1H-pyrazol-1-yl)phenyl]propan-2-ol as an orange solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-ba57019b92ad44a98a8232927d7ee502
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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