2,2,2-Trifluoroethanesulfonyl chloride → N-(3-(4-Cyanophenyl)phenyl)-N-(2,2,2-trifluoroethylsulfonyl)pyrid-3-ylmethylamine

HRID 392458Notes

Reaction equation

HRID 392458 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([NH:15][CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1)#[N:2].[F:23][C:24]([F:31])([F:30])[CH2:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl.C(OCC)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]([N:15]([CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[S:26]([CH2:25][C:24]([F:31])([F:30])[F:23])(=[O:28])=[O:27])[CH:12]=[CH:13][CH:14]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 69880749N-(3-(4-Cyanophenyl)phenyl)pyrid-3-ylmethylamine

Product 1

HCID 23521688N-(3-(4-Cyanophenyl)phenyl)-N-(2,2,2-trifluoroethylsulfonyl)pyrid-3-ylmethylamine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-(3-(4-cyanophenyl)phenyl)pyrid-3-ylmethylamine (255 mg, 0.894 mmol) in 8 ml dichloromethane/2 ml pyridine was treated with 2,2,2-trifluoroethylsulfonyl chloride in 3 portions of 171 mg (0.94 mmol) over 1 h at 45° C. The solution was cooled and diluted with 60 ml diethyl ether and washed successively with water and saturated sodium bicarbonate solution. The organics were separated, dried over sodium sulfate, filtered, and concentrated to an oil. The oil was purified by radial chromatography on a 2 micron silica plate eluting with 2 to 4% methanol/dichloromethane to afford the title compound. 1H NMR: 8.65 (bs,1H), 8.42 (bs,1H), 7.85 (m,1H), 7.75 (d,2H,J=8 Hz), 7.58 (d,2H,J=8 Hz), 7.30-7.55 (m,5H), 5.02 (s,2H), 3.78 (q,2H,J=8 Hz). MS calcd. 431.44; MS (M+1) 432.1.

Workup

  1. temperatureThe solution was cooled
  2. washwashed successively with water and saturated sodium bicarbonate solution
  3. customThe organics were separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThe oil was purified by radial chromatography on a 2 micron silica plate
  8. washeluting with 2 to 4% methanol/dichloromethane

Sources & evidence

ORD record
ord-23f10e7c6f7d4be9a58ebc3a85ef1c0e
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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