Allyl bromide → 2-(1-Allyl-5-trifluoromethyl-1H-indazol-3-yl)-isoindole-1,3-dione

HRID 2089230Notes

Reaction equation

HRID 2089230 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22].C([O-])([O-])=O.[K+].[K+].[CH2:31](Br)[CH:32]=[CH2:33]>CC(C)=O>[CH2:33]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([C:2]([F:23])([F:1])[F:24])=[CH:11][CH:10]=2)[C:6]([N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[N:7]1)[CH:32]=[CH2:31]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 585488622-(5-Trifluoromethyl-1H-indazol-3-yl)-isoindole-1,3-dione

Product 1

HCID 585488592-(1-Allyl-5-trifluoromethyl-1H-indazol-3-yl)-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(5-Trifluoromethyl-1H-indazol-3-yl)-isoindole-1,3-dione (500 mg, 1.51 mmol), K2CO3 (313 mg, 2.26 mmol) and allyl bromide (365 mg, 3.02 mmol) in acetone (10 mL) were heated to reflux overnight. The reaction was filtered, and the residue was concentrated and purified by silica gel column chromatography using hexanes:ethyl acetate 2:1 to give the title compound as white solid.

Workup

  1. temperatureto reflux overnight
  2. filtrationThe reaction was filtered
  3. concentrationthe residue was concentrated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-bb13fa88d3624b88a62ae5e32cab2fb9
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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