Isopropyl iodide → [4-(benzyloxy)phenyl][1-isopropyl-7-(trifluoromethyl)-1H-indazol-3-yl]methanone

HRID 1817496Notes

Reaction equation

HRID 1817496 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:25]3[C:20](=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:22]=[CH:23][CH:24]=3)[NH:19][N:18]=2)=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH:33]([CH3:35])[CH3:34]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([C:17]2[C:25]3[C:20](=[C:21]([C:26]([F:29])([F:27])[F:28])[CH:22]=[CH:23][CH:24]=3)[N:19]([CH:33]([CH3:35])[CH3:34])[N:18]=2)=[O:16])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 178519713HCID 178519713, compound

Product 1

HCID 69061008[4-(benzyloxy)phenyl][1-isopropyl-7-(trifluoromethyl)-1H-indazol-3-yl]methanoneYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of [4-(benzyloxy)phenyl](7-trifluoromethyl-1H-indazol-3-yl)methanone (0.20 g, 0.5 mmol) in 3 mL DMF was added in one portion sodium hydride (0.020 g, 0.5 mmol, 60% in oil). After the gas evolution ceased, 2-iodopropane (0.075 mL, 0.75 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 provided 0.18 g of the title compound which was used directly in the following step.

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

Sources & evidence

ORD record
ord-0081f823199e4a138a49c9f689b7f70d
Source dataset
uspto-grants-2009_10
Patent number
US07598286B2

Reaction notes

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