3-Chloro-5-(4-methoxy-2-trifluoromethyl-phenylamino)-pyridine-2-carbonitrile → (6-Aminomethyl-5-chloro-pyridin-3-yl)-(4-methoxy-2-trifluoromethyl-phenyl)-amine

HRID 1428222Notes

Reaction equation

HRID 1428222 reaction equation
[Cl:1][C:2]1[C:3]([C:21]#[N:22])=[N:4][CH:5]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[C:17]([F:20])([F:19])[F:18])[CH:7]=1>C(O)C.Cl.[Pd].C>[NH2:22][CH2:21][C:3]1[N:4]=[CH:5][C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[C:17]([F:20])([F:18])[F:19])=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 1

HCID 667655693-Chloro-5-(4-methoxy-2-trifluoromethyl-phenylamino)-pyridine-2-carbonitrile

Product 1

HCID 66765570(6-Aminomethyl-5-chloro-pyridin-3-yl)-(4-methoxy-2-trifluoromethyl-phenyl)-amine

Reagents, catalysts & solvents 3

HCID 14818447PalladiumcarbonCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 3-chloro-5-(4-methoxy-2-trifluoromethyl-phenylamino)-pyridine-2-carbonitrile (0.64 mmol) in 10 mL ethanol and 0.1 mL hydrochloric acid (37%) was combined with 30 mg of Pd/charcoal (10%) and hydrogenated with stirring at ambient temperature. Then the catalyst was filtered off and the solution was evaporated down. The product thus obtained was reacted further without purification.

Workup

  1. filtrationThen the catalyst was filtered off
  2. customthe solution was evaporated down
  3. customThe product thus obtained
  4. customwas reacted further without purification

Sources & evidence

ORD record
ord-552ed336794f4229b3515edc27ad27ca
Source dataset
uspto-grants-2015_01
Patent number
US08937073B2

Reaction notes

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