Pyridine → HCID 23521659, compound

HRID 392439Notes

Reaction equation

HRID 392439 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:5]=[C:6]([NH:10][CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:8][CH:9]=1.N1C=CC=CC=1.[F:26][C:27]([F:34])([F:33])[CH2:28][S:29](Cl)(=[O:31])=[O:30]>ClC(Cl)C>[F:19][C:2]([F:18])([F:1])[O:3][C:4]1[CH:5]=[C:6]([N:10]([CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[S:29]([CH2:28][C:27]([F:34])([F:33])[F:26])(=[O:31])=[O:30])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 28490223HCID 28490223, compound

Product 1

HCID 23521659HCID 23521659, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

N-(3-trifluoromethoxyphenyl)pyrid-3-ylmethylamine(0.270 g, 1 mmol) and pyridine were dissolved in dichloroethane (2 ml). The solution was cooled in an ice-bath. To the solution was added 2,2,2-trifluoroethylsulfonyl chloride (0.274 g, 1.5 mmol). The mixture was stirred at room temperature overnight. Upon removing solvent, the residue was dissolved in water and extracted with EtOAc. The organic phase was washed with brine concentrated. The residue was chromatographed to afford the title compound. 1H NMR: 8.42 (d,1H,J=6.4 Hz), 8.20 (d,1H,J=2.0 Hz), 7.57 (d,1H,J=9.8 Hz), 7.40-6.85 (m,5H), 4.81 (s,2H), 3.72 (q,2H, J=7.8 Hz). MS calcd 414.1; MS (M+1) 415.1.

Workup

  1. temperatureThe solution was cooled in an ice-bath
  2. customUpon removing solvent
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with EtOAc
  5. washThe organic phase was washed with brine
  6. concentrationconcentrated
  7. customThe residue was chromatographed

Sources & evidence

ORD record
ord-b40a43d09d1a454bb29eaa0d36d1c6fe
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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