Dimethylformamide → 4-Bromo-1-isopropyl-1H-pyrazole

HRID 2176530Notes

Reaction equation

HRID 2176530 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[N:10][NH:11][CH:12]=1.CN(C=O)C.I[CH:19]([CH3:21])[CH3:20]>CCOC(C)=O>[Br:7][C:8]1[CH:9]=[N:10][N:11]([CH:19]([CH3:21])[CH3:20])[CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 163754-Bromopyrazole

Product 1

HCID 223292004-Bromo-1-isopropyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A sealable vessel was charged with potassium carbonate (3.76 g, 27.2 mmol), 4-bromo-1H-pyrazole (4.00 g, 27.2 mmol), and 10 mL DMF. To this mixture, 2-iodopropane (3.27 ml, 32.7 mmol) was added and the vessel sealed. The mixture was heated at 80 C for 16 h and allowed to cool to rt. The mixture was diluted with EtOAc, extracted with water, water, sat NaHCO3, and the organic layer dried over Na2SO4, filtered and evaporated. The mixture was purified via flash chromatography using a EtOAc in CH2Cl2 gradient. The desired compound (as determined by TLC, I2 stain) was collected as a colorless liquid.

Workup

  1. customthe vessel sealed
  2. temperatureThe mixture was heated at 80 C for 16 h
  3. extractionextracted with water, water
  4. dry with materialthe organic layer dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe mixture was purified via flash chromatography
  8. customThe desired compound (as determined by TLC, I2 stain) was collected as a colorless liquid

Sources & evidence

ORD record
ord-d467584d0c814712917fc38bee02121b
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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