Allyl bromide → HCID 57890016, compound

HRID 735412Notes

Reaction equation

HRID 735412 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[C:13]1[C:21]2[C:16](=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:18]=[CH:19][CH:20]=2)[NH:15][N:14]=1.[CH2:26](Br)[CH:27]=[CH2:28]>CN(C=O)C>[CH2:28]([N:14]1[C:13]([C:6]2[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:5]=2[O:4][CH3:3])=[C:21]2[C:16]([C:17]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:19]=[CH:20]2)=[N:15]1)[CH:27]=[CH2:26]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 178489136HCID 178489136, compound

Product 1

HCID 57890016HCID 57890016, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 0.025 g, 1.04 mmol) was added in one portion to a solution of 3-(2,4-dimethoxyphenyl)-7-(trifluoromethyl)-1H-indazole (0.150 g, 0.49 mmol) in DMF. After the gas evolution ceased, allyl bromide (0.07 mL, 0.7 mmol) was added and the reaction mixture was stirred at ambient temperature to 50° C. overnight. The cool reaction mixture was partitioned with EtOAc and 1 N HCl. The organic phase was washed with brine and dried (Na2SO4). The resulting residue was purified by flash chromatography or by HPLC chromatography through silica gel columns, 150×12 mm (Biotage, Charlottesville, Va.), at 10 mL/min with methyl-t-butyl ether/hexane (gradient elution, 1:9 to 1:1) to give the title compound (0.062 g) as a white solid.

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. customThe resulting residue was purified by flash chromatography or by HPLC chromatography through silica gel columns, 150×12 mm (Biotage, Charlottesville, Va.), at 10 mL/min with methyl-t-butyl ether/hexane (gradient elution, 1:9 to 1:1)

Sources & evidence

ORD record
ord-8707cea3304043dab29cbcd18a953168
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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