2,4,6-Trifluorobenzyl bromide → 2-(2,4-Difluorobenzyl)-3-pyridin-2-YL-7-(trifluoromethyl)-2H-indazole

HRID 735461

Reaction equation

HRID 735461 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:8][N:9]=[C:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]([F:19])([F:18])[F:17].[F:20][C:21]1[CH:28]=[C:27]([F:29])[CH:26]=[C:25](F)[C:22]=1[CH2:23]Br>CN(C=O)C>[F:20][C:21]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:22]=1[CH2:23][N:8]1[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[C:15]2[C:10]([C:11]([C:16]([F:19])([F:17])[F:18])=[CH:12][CH:13]=[CH:14]2)=[N:9]1

Participants

4

Reactant 2

HCID 27770592,4,6-Trifluorobenzyl bromideHCID 67021302HCID 67021302, compound

Product 1

HCID 670212302-(2,4-Difluorobenzyl)-3-pyridin-2-YL-7-(trifluoromethyl)-2H-indazoleYield 12.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Then a solution of 3-pyridin-2-yl-7-(trifluoromethyl)-2H-indazole (0.183 g, 0.7 mmol) and 2,4,6-trifluorobenzyl bromide (0.203 g, 0.9 mmol) in DMF (5 mL) was heated at 120° C. After 5 days, the reaction mixture was partitioned with EtOAc and water. Organics were washed with water (3×), then brine and dried over MgSO4, then stripped and the resulting crude product was flashed by reverse phase HPLC to afford the title compound (0.033 g, 5%).

Workup

  1. customthe reaction mixture was partitioned with EtOAc and water
  2. washOrganics were washed with water (3×)
  3. dry with materialbrine and dried over MgSO4

Sources & evidence

ORD record
ord-ab37a66d1bf74b66a42a1dec0c0a2e33
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Linked notes

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