Trifluoroacetic acid → (2-Chloro-benzyl)-(6-fluoro-pyridin-2-yl)-amine

HRID 1775149Notes

Reaction equation

HRID 1775149 reaction equation
[F:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[Cl:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH2:12][NH:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 69962-ChlorobenzaldehydeHCID 12052TriethylsilaneHCID 27613996-Fluoropyridin-2-amine

Product 1

HCID 57963158(2-Chloro-benzyl)-(6-fluoro-pyridin-2-yl)-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To 6-fluoro-pyridin-2-ylamine (14, 2.47 g, 22.0 mmol) in 60.0 mL of acetonitrile, 2-chloro-benzaldehyde (15, 3.09 g, 22.0 mmol), triethylsilane (14.0 mL, 87.6 mmol) and trifluoroacetic acid (7.00 mL, 90.9 mmol) were added. The reaction was stirred at 80° C. for 4 hours, then solvents removed under vacuum, and the residue was combined with aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound, which was used in the next step without further purification. MS (ESI) [M+H+]+=272.1.

Workup

  1. customsolvents removed under vacuum
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-ce633b71dbb64bd5a6ef180d018c1e3a
Source dataset
uspto-grants-2016_02
Patent number
US09260437B2

Reaction notes

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