2-Pyridinemethanamine → HCID 68517676, compound

HRID 386744Notes

Reaction equation

HRID 386744 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:22]([F:25])([F:24])[F:23])[O:13][N:12]=[C:11]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C[Si]([C:38]#[N:39])(C)C.Cl([O-])(=O)(=O)=O.[Li+]>O1CCCC1.C(OC)(C)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:22]([F:25])([F:24])[F:23])[O:13][N:12]=[C:11]([C:14]3[CH:21]=[CH:20][C:17]([CH:18]([NH:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[C:38]#[N:39])=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 4

HCID 195092-PyridinemethanamineHCID 82115Trimethylsilyl cyanideHCID 23665649Lithium perchlorateHCID 86643376HCID 86643376, compound

Product 1

HCID 68517676HCID 68517676, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]benzaldehyde (0.30 g), 2-aminomethylpyridine (0.09 g) and trimethylsilylcyanide (0.08 g) in tetrahydrofuran (5 mL), lithium perchlorate (0.8 g) was added, and the mixture was then stirred for one hour at room temperature. After the reaction mixture 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 then purified by silica gel chromatography to obtain {4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]phenyl}[(pyridin-2-ylmethyl)amino]acetonitrile (0.15 g).

Workup

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

Sources & evidence

ORD record
ord-d26afe71706344cea4f43cc72e0f2cdd
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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