HCID 76619013, compound → HCID 57814303, compound

HRID 2406607Notes

Reaction equation

HRID 2406607 reaction equation
CO[N:3]=[C:4]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1>C(O)(C(F)(F)F)=O.[Pd]>[F:18][C:14]1[CH:13]=[C:12]([CH:4]([NH2:3])[CH2:5][C:6]2[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 76619013HCID 76619013, compound2×

Product 1

HCID 57814303HCID 57814303, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1-(3-fluorophenyl)-2-(pyridin-4-yl)ethanone O-methyl oxime, (19) (1.86 g) in TFA (20 mL) was reduced by the action of 10% Pd/C (186 mg) under H2 at 50 psi for 12 h at rt. The mixture was filtered through Celite and freed of solvent under reduced pressure. The residue was basified using 6N KOH. The aqueous layer was extracted with EtOAc (3×, 500 mL). The pooled organic layer was dried over magnesium sulfate. The mixture was filtered. The solvents were removed under vacuum gave 1-(3-fluorophenyl)-2-(pyridin-4-yl)ethanamine, (20): as a solid (1.6 g, 97% yield).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. extractionThe aqueous layer was extracted with EtOAc (3×, 500 mL)
  3. dry with materialThe pooled organic layer was dried over magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customThe solvents were removed under vacuum

Sources & evidence

ORD record
ord-031ac83aad7e4845aaa2e27f41d24cf0
Source dataset
uspto-grants-2014_08
Patent number
US08809379B2

Reaction notes

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