Dimethylformamide → HCID 67168187, compound

HRID 1517598Notes

Reaction equation

HRID 1517598 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:11])=[N:8][NH:9][CH:10]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].FN1C=C[CH:22]=[CH:21][CH:20]1[Br:25].[CH3:26][N:27]([CH3:30])C=O>O>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:11])=[N:8][N:9]([C:26]2[C:20]([Br:25])=[CH:21][CH:22]=[CH:30][N:27]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 86653545HCID 86653545, compoundHCID 178469911HCID 178469911, compound

Product 1

HCID 67168187HCID 67168187, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To the solution of 3-methyl-pyrazole-4-carboxylic acid ethyl ester (2.0 g, 13 mmol) in dry dimethylformamide (30 mL) is added potassium carbonate (7.2 g, 52 mmol) at room temperature. The reaction mixture is stirred at 40° C. for 30 min and then 1-fluoro-2-bromopyridine (3.0 g, 17 mmol) is added. The reaction mixture is stirred at 70° C. for 4 h. The reaction mixture is cooled to room temperature, diluted with water and then extracted with ethyl acetate. The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated under reduce pressure. The crude mixture was purified by chromatography on silica gel eluting with hexane/ethyl acetate (85:15, 80:20) to yield 3.2 g (79%) of 1-(3-bromo-pyridin-2-yl)-3-methyl-pyrazole-4-carboxylic acid ethyl ester. MS (m/z): 312 (M+3), 310 (M+1).

Workup

  1. stirringThe reaction mixture is stirred at 70° C. for 4 h
  2. temperatureThe reaction mixture is cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude mixture was purified by chromatography on silica gel eluting with hexane/ethyl acetate (85:15, 80:20)

Sources & evidence

ORD record
ord-d0962d93824942bd937f7316ba1af960
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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