Bromocyclopentane → 1-cyclopentyl-4-iodo-1H-pyrazole

HRID 64081

Reaction equation

HRID 64081 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>CN(C=O)C>[CH:14]1([N:4]2[CH:3]=[C:2]([I:1])[CH:6]=[N:5]2)[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 770224-Iodopyrazole

Product 1

HCID 567773301-cyclopentyl-4-iodo-1H-pyrazoleYield 89.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodo-1H-pyrazole (5 g, 25.78 mmol, 1.0 eq.) in DMF (25 ml) were added K2CO3 (8.908 g, 64.45 mmol, 2.5 eq.) and bromocyclopentane (4.96 g, 33.51 mmol, 1.3 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 give the product in 89.5% yield. 1H NMR (300 MHz, CDCl3): δ 7.49 (s, 1H), 7.45 (s, 1H), 4.66-4.62 (m, 1H), 2.17-2.02 (m, 1H), 2.00-1.96 (m, 2H), 1.93-1.78 (m, 2H), 1.73-1.67 (m, 2H). LC-MS (ESI): Calculated mass: 262; Observed mass: 263 [M+H]+ (rt: 1.57 min).

Workup

  1. customThe mixture was quenched
  2. extractionextracted as in Intermediate Example 5(a)
  3. distillationThe solvent was distilled off
  4. customto give the product in 89.5% yield
  5. custom263 [M+H]+ (rt: 1.57 min)

Sources & evidence

ORD record
ord-58880dbf79124678b073a50a8366605f
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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