Potassium Carbonate → HCID 86711961, compound

HRID 1475270Notes

Reaction equation

HRID 1475270 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[O:9][N:8]=2)[NH:5][N:6]=1.C([O-])([O-])=O.[K+].[K+].[Br:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36]Br)[CH:31]=1>CN(C=O)C.O>[Br:29][C:30]1[CH:31]=[C:32]([CH:33]=[CH:34][CH:35]=1)[CH2:36][N:6]1[C:2]([CH3:1])=[N:3][C:4]([C:7]2[CH:11]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:16][CH:17]=3)[O:9][N:8]=2)=[N:5]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699793-Bromobenzyl bromideHCID 178434567HCID 178434567, compound

Product 1

HCID 86711961HCID 86711961, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-(5-methyl-2H-1,2,4-triazol-3-yl)-5-(4-(trifluoromethoxy)phenyl) isoxazole (400 mg, 1.3 mmol) and K2CO3 (445 mg, 3.3 mmol) in DMF (5 mL) was added 1-bromo-3-(bromomethyl)benzene (323 mg, 1.3 mmol). The mixture was stirred at RT for 2 h, then diluted with H2O (30 mL) and extracted with EtOAc (2×40 mL). The combined organic layers were washed with H2O (20 mL) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Petroleum ether:EA=1:1) to afford the title compound as a light yellow solid (350 mg, 56.6%). MS (ES+) C20H14BrF3N4O2 requires: 478. found: 479 [M+H]+.

Workup

  1. extractionextracted with EtOAc (2×40 mL)
  2. washThe combined organic layers were washed with H2O (20 mL)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (Petroleum ether:EA=1:1)

Sources & evidence

ORD record
ord-9fb352bd28134e2c84d83d010d7efb21
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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