Water → HCID 63811807, compound

HRID 2067934Notes

Reaction equation

HRID 2067934 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.F[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 127492-MethylimidazoleHCID 27746352-Fluoro-5-methylpyridine

Product 1

HCID 63811807HCID 63811807, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Methylimidazole (2.0 g, 24 mmol) and 2-Fluoro-5-methylpyridine (5.41 g, 49 mmol) were dissolved in 40 ml dimethyl formamide. Cesium carbonate (23.8 g, 73 mmol) was added, and the reaction mixture was stirred at 100° C. overnight. The reaction mixture was poured into 100 mL water and extracted three times with ethyl acetate (150 mL each). The combined organic extracts were dried with sodium sulfate, filtered and evaporated. The desired compound was obtained as a brown oil (4.0 g, 95%), MS: m/e=174.1 (M+H+).

Workup

  1. extractionextracted three times with ethyl acetate (150 mL each)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-fc4b328de8564f3688b4adec601bfd60
Source dataset
uspto-grants-2012_10
Patent number
US08293916B2

Reaction notes

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