3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(1-methylethenyl)benzonitrile → 3-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(1-methylethyl)benzonitrile

HRID 1874930Notes

Reaction equation

HRID 1874930 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:22])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([C:19]([CH3:21])=[CH2:20])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1>C(O)C.[Pt](=O)=O>[NH2:1][CH2:2][C:3]1[C:4]([F:22])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([CH:19]([CH3:20])[CH3:21])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 684871183-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(1-methylethenyl)benzonitrile

Product 1

HCID 684876543-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(1-methylethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(1-methylethenyl)benzonitrile (0.067 g, 0.212 mmol) dissolved in ethanol (10 mL) was treated with platinum(IV) oxide (0.050 g, 0.220 mmol) under hydrogen (1 atm) at 25° C. for 4 h. LC-MS indicates ˜90% conversion but multiple impurities are present. The reaction mixture was filtered through Celite and concentrated to give crude 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(1-methylethyl)benzonitrile as an amber oil which was used without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-1fdd3903687e4686a9d4dd72f6ee3d8f
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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