Tetrahydrofuran → 2-(4-bromo-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridine

HRID 331163Notes

Reaction equation

HRID 331163 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.O1CCCC1.CS([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[N:3]=[CH:4][N:5]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 27614382-Methylsulfonyl-5-trifluoromethylpyridineHCID 178418934HCID 178418934, compound

Product 1

HCID 683804802-(4-bromo-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridineYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

A dried pressure tube was charged with 4-bromo-1H-imidazole (100 mg, 667 μmol), tetrahydrofuran (3 ml), N,N-dimethylformamide (2 ml), 2-(methylsulfonyl)-5-(trifluoromethyl)pyridine (150 mg, 667 μmol), and cesium carbonate (261 mg, 800 μmol). The tube was sealed and heated at 105° C. for 16 hours. For the workup, the reaction mixture was evaporated at reduced pressure and the residue directly purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 60:30 as the eluent. The 2-(4-bromo-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridine (167 mg, 86% yield) was obtained as a crystalline white solid. MS (ISP): m/z=292.0 [M+H]+ and 294.2 [M+2+H]+.

Workup

  1. customThe tube was sealed
  2. customFor the workup, the reaction mixture was evaporated at reduced pressure
  3. customthe residue directly purified by chromatography on silica gel using a gradient of heptane/ethyl acetate=100:0 to 60:30 as the eluent

Sources & evidence

ORD record
ord-2b70773ccb3c4d49b0ad0d034bf010b0
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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