Potassium Carbonate → 4-Bromo-1-(cyclopropylmethyl)-1H-pyrazole

HRID 64053

Reaction equation

HRID 64053 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:14][CH:15]1[CH2:17][CH2:16]1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:14][CH:15]2[CH2:17][CH2:16]2)[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 163754-BromopyrazoleHCID 81503Bromomethylcyclopropane

Product 1

HCID 510722584-Bromo-1-(cyclopropylmethyl)-1H-pyrazoleYield 109.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-1H-pyrazole (0.1 g, 0.68 mmol) in DMF (20 ml) were added K2CO3 (0.19 g, 1.36 mmol, 2 eq.) and (bromomethyl)cyclopropane (92 mg, 0.68 mmol, 1 eq.). The mixture was stirred at RT for 4 h. The mixture was quenched and extracted as in Intermediate Example 5(c). The solvent was distilled off to afford the crude product (0.15 g).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Intermediate Example 5(c)
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-a167ce228617490a96ee8259ff7c99af
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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