Potassium Carbonate → HCID 86711955, compound

HRID 1475264Notes

Reaction equation

HRID 1475264 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:14][CH:13]=3)[CH:8]=2)[N:3]=1.[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30]Br)[CH:25]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[Br:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:28][CH:29]=1)[CH2:30][N:6]1[C:2]([CH3:1])=[N:3][C:4]([C:7]2[O:11][N:10]=[C:9]([C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:16][CH:17]=3)[CH:8]=2)=[N:5]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699793-Bromobenzyl bromideHCID 86711953HCID 86711953, compound

Product 1

HCID 86711955HCID 86711955, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(5-methyl-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-isoxazole (257 mg, 0.83 mmol) and 1-bromo-3-(bromomethyl)benzene (206 mg, 0.83 mmol) in DMF (20 mL), was added K2CO3 (286 mg, 2.07 mmol). The mixture was stirred at RT for 16 h, then diluted with H2O (50 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were washed with H2O (20 mL) and brine (20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure; the residue was purified by silica gel chromatography (Petroleum ether:EtOAc=1:1) to give the title compound as a white solid (230 mg, 58%). MS (ES+) C20H14BrF3N4O2 requires: 478. found: 479 [M+H]+.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined organic layers were washed with H2O (20 mL) and brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (Petroleum ether:EtOAc=1:1)

Sources & evidence

ORD record
ord-3a4bff7f6a8c47a69c1b69544675b8bd
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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