Bromocyclopentane → HCID 69060133, compound

HRID 1817501Notes

Reaction equation

HRID 1817501 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[C:19]3[C:14](=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH:26]1(Br)[CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C=O)C>[CH:26]1([N:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]([F:23])([F:21])[F:22])[C:11]([C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:10])=[N:12]2)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 178490436HCID 178490436, compound

Product 1

HCID 69060133HCID 69060133, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of [3-(methoxy)phenyl](7-trifluoromethyl-1H-indazol-3-yl)methanone (0.27 g, 0.85 mmol) in 5 mL DMF was added in one portion sodium hydride (0.034 g, 0.85 mmol, 60% in oil). After the gas evolution ceased, cyclopentyl bromide (0.107 mL, 1.0 mmol) was added and the reaction was stirred at ambient to 50° C. for 24 hours. The cool reaction mixture was partitioned with EtOAc and 1 N HCl. The organic phase was washed with brine and dried (Na2SO4). Removal of the solvent in vacuo afforded the crude product which was purified by flash chromatography (silica gel, hexane/EtOAC, 9:1) to give the title compound (0.250 g) as an oil.

Workup

  1. customThe cool reaction mixture
  2. customwas partitioned with EtOAc and 1 N HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent in vacuo
  6. customafforded the crude product which
  7. customwas purified by flash chromatography (silica gel, hexane/EtOAC, 9:1)

Sources & evidence

ORD record
ord-a20e288f76414338a2aa31edaa36ba28
Source dataset
uspto-grants-2009_10
Patent number
US07598286B2

Reaction notes

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