Potassium Carbonate → HCID 86643373, compound

HRID 386733Notes

Reaction equation

HRID 386733 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:14][C:13]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)([C:15]([F:18])([F:17])[F:16])[O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[CH2:8]Br.[NH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OC)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[CH2:14][C:13]([C:19]3[CH:20]=[C:21]([Cl:26])[CH:22]=[C:23]([Cl:25])[CH:24]=3)([C:15]([F:17])([F:18])[F:16])[O:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][NH:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 195092-PyridinemethanamineHCID 866433713-[3-Bromo-4-(bromomethyl)phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole

Product 1

HCID 86643373HCID 86643373, compoundYield 52.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 3-[3-bromo-4-(bromomethyl)phenyl]-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (1.8 g), 2-aminomethylpyridine (0.38 g) and potassium carbonate (0.97 g) in acetonitrile (20 mL) was heated to reflux for 3 hours. After the reaction solution was diluted with t-butylmethylether, the solution was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography to yield 1-{2-bromo-4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]phenyl}-N-(pyridin-2-ylmethyl)methanamine (1.0 g).

Workup

  1. temperatureto reflux for 3 hours
  2. washthe solution was washed with water and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-46fef948e31c479db5ce0283a97cb74d
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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