Allyl bromide → HCID 89620465, compound

HRID 1499996Notes

Reaction equation

HRID 1499996 reaction equation
[CH3:1][C:2]1[C:16]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:14]=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[C:11]([CH3:12])=[N:10][O:9][N:8]=1)=[O:5].[CH2:25](Br)[CH:26]=[CH2:27].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH2:27]([N:6]([C:7]1[C:11]([CH3:12])=[N:10][O:9][N:8]=1)[C:4](=[O:5])[C:3]1[CH:13]=[CH:14][C:15]([C:21]([F:24])([F:23])[F:22])=[C:16]([S:17]([CH3:20])(=[O:19])=[O:18])[C:2]=1[CH3:1])[CH:26]=[CH2:25]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 117739384HCID 117739384, compound

Product 1

HCID 89620465HCID 89620465, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

150 mg (0.413 mmol) of 2-methyl-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(methylsulfonyl)-4-(trifluoromethyl)benzamide and 50 mg (0.413 mmol) of allyl bromide are dissolved in 5 ml of N,N-dimethylformamide, and 0.057 mg (0.413 mmol) of potassium carbonate is added. The reaction mixture is stirred at 80° C. for 8 h and taken up in 5 ml of water and extracted twice with 10 ml each time of dichloromethane. The organic phase is dried over Na2SO4 and concentrated. The residue is purified by means of preparative HPLC (acetonitrile, water). Yield 160 mg (86%).

Workup

  1. extractionextracted twice with 10 ml each time of dichloromethane
  2. dry with materialThe organic phase is dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue is purified by means of preparative HPLC (acetonitrile, water)

Sources & evidence

ORD record
ord-82b9acddfc144ce587f73ac6c10ad7dd
Source dataset
uspto-grants-2015_12
Patent number
US09204650B2

Reaction notes

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