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

HRID 509942Notes

Reaction equation

HRID 509942 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 (43, 2.47 g, 22.0 mmol) in 60.0 mL of acetonitrile, 2-chloro-benzaldehyde (44, 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-fb00c30bd8b2476d8ce67d42687d072a
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

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