2,2,2-Trifluoroethanesulfonyl chloride → N-(5-(3-chloro-4-cyanophenyl)pyridin-3-yl)-2,2,2-trifluoroethanesulfonamide

HRID 1897757Notes

Reaction equation

HRID 1897757 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([Cl:16])[CH:9]=2)[CH:5]=[N:6][CH:7]=1.[F:17][C:18]([F:25])([F:24])[CH2:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1>[Cl:16][C:10]1[CH:9]=[C:8]([C:4]2[CH:3]=[C:2]([NH:1][S:20]([CH2:19][C:18]([F:25])([F:24])[F:17])(=[O:22])=[O:21])[CH:7]=[N:6][CH:5]=2)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]

Participants

4

Reactant 2

HCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 595783904-(5-Amino-pyridin-3-yl)-2-chloro-benzonitrile

Product 1

HCID 49819664N-(5-(3-chloro-4-cyanophenyl)pyridin-3-yl)-2,2,2-trifluoroethanesulfonamideYield 27.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

According to General Sulfonylation Procedure 2 in Example 1, to a solution of 4-(5-amino-pyridin-3-yl)-2-chloro-benzonitrile (20 mg, 87 μmol, 1 eq) in anhydrous pyridine (500 μl) was added 2,2,2-trifluoro-ethanesulfonyl chloride (10.6 μl, 96 μmol, 1.1 eq). The product was purified by preparative TLC, the plate was eluted with dichloromethane/methanol 95/5, to give N-(5-(3-chloro-4-cyanophenyl)pyridin-3-yl)-2,2,2-trifluoroethanesulfonamide (9 mg, >95% purity, yield: 27.6%). The isolated product was lyophilized and identified by LC-MS (system 1) and NMR (system 3): ESI-MS m/z: 376 [M+H]+, retention time=2.10 min, 1H NMR (500 MHz, DMSO-d6) δ ppm 4.75 (q, J=9.66 Hz, 2H) 7.87-7.91 (m, 2H) 8.11-8.14 (m, 1H) 8.14 (s, 1H) 8.46 (d, J=2.44 Hz, 1H) 8.74 (d, J=1.83 Hz, 1H) 10.94 (br. s., 1H).

Workup

  1. customThe product was purified by preparative TLC
  2. washthe plate was eluted with dichloromethane/methanol 95/5

Sources & evidence

ORD record
ord-7b8a239912c44c7f86c6dda28a9ceb59
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

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