2-Bromopropane → 4-Bromo-1-isopropyl-1H-pyrazole

HRID 64074Notes

Reaction equation

HRID 64074 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:14]([CH3:16])[CH3:15]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH:14]([CH3:16])[CH3:15])[CH:6]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 163754-Bromopyrazole

Product 1

HCID 223292004-Bromo-1-isopropyl-1H-pyrazoleYield 76.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-1H-pyrazole (5 g, 34.24 mmol, 1.0 eq) in DMF were added K2CO3 (11.83 g, 85.60 mmol, 2.5 eq.) and 2-bromopropane (6.31 g, 51.36 mmol, 1.5 eq.) The mixture was stirred at RT for 12 h. The mixture was quenched and extracted as in Intermediate Example 5(a). The solvent was distilled off to afford the product in 76.9% yield (5.0 g).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Intermediate Example 5(a)
  3. distillationThe solvent was distilled off
  4. customto afford the product in 76.9% yield (5.0 g)

Sources & evidence

ORD record
ord-a86fad0b7d03455fba27fb35c0741e76
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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