Benzyl Bromide → 2-benzyl-3-(4-methoxy-phenyl)-7-trifluoromethyl-2H-indazole

HRID 735407Notes

Reaction equation

HRID 735407 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[NH:11][N:10]=2)=[CH:5][CH:4]=1.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OCC)(=O)C>CN(C=O)C>[CH2:22]([N:10]1[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[C:17]2[C:12]([C:13]([C:18]([F:21])([F:19])[F:20])=[CH:14][CH:15]=[CH:16]2)=[N:11]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 178489134HCID 178489134, compound

Product 1

HCID 115960792-benzyl-3-(4-methoxy-phenyl)-7-trifluoromethyl-2H-indazoleYield 79.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-(4-methoxy-phenyl)-7-trifluoromethyl-1H-indazole (59 mg, 0.2 mmol) in 0.5 ml DMF were added 72 μl of benzyl bromide (0.6 mmol). The reaction mixture was heated overnight at 120° C. After cooling to room temperature, ethyl acetate was added and the solution was washed three times with brine. The organic layer was dried over MgSO4 and concentrated. Column chromatography (n-heptane/ethyl acetate, 70:30 as eluent) afforded 61 mg of pure product.

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe solution was washed three times with brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6122a12572e74474b1d6b2e253ddce98
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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