Methyl 2-(6-cyano-5-fluoropyridin-3-yl)-6-fluorobenzoate → Methyl 2-[6-(aminomethyl)-5-fluoropyridin-3-yl]-6-fluorobenzoate

HRID 1711485Notes

Reaction equation

HRID 1711485 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:4]=1[F:20])#[N:2]>N.CO.[Ni]>[NH2:2][CH2:1][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:4]=1[F:20]

Participants

4

Reactant 1

HCID 21075884Methyl 2-(6-cyano-5-fluoropyridin-3-yl)-6-fluorobenzoate

Product 1

HCID 21075883Methyl 2-[6-(aminomethyl)-5-fluoropyridin-3-yl]-6-fluorobenzoateYield 86.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

To a stirred solution of the above ester (0.75 g, 2.7 mmol) in NH3/MeOH (5 mL, 2.0 M) was added Raney 2800 nickel (slurry in water). The mixture was stirred under a H2 atmosphere (balloon) at room temperature for 6 hours. The mixture was then filtered through glass filter paper, washing with additional MeOH. The resultant solution was concentrated under vacuum and azeotroped three times with toluene to provide crude title compound (0.65 g, 2.34 mmol).

Workup

  1. filtrationThe mixture was then filtered through glass
  2. filtrationfilter paper
  3. washwashing with additional MeOH
  4. concentrationThe resultant solution was concentrated under vacuum
  5. customazeotroped three times with toluene

Sources & evidence

ORD record
ord-b67283e28ac84eacb795c4b32cc94867
Source dataset
uspto-grants-2010_09
Patent number
US07790754B2

Reaction notes

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