4-Ethylbenzene-1-sulfonyl chloride → N-[5-(3-chloro-4-cyano-phenyl)-pyridin-3-yl]-4-ethyl-benzenesulfonamide

HRID 1897753Notes

Reaction equation

HRID 1897753 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.[CH2:17]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)[CH3:18]>N1C=CC=CC=1>[Cl:16][C:10]1[CH:9]=[C:8]([C:4]2[CH:3]=[C:2]([NH:1][S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH2:17][CH3:18])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[CH:7]=[N:6][CH:5]=2)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]

Participants

4

Reactant 2

HCID 5709594-Ethylbenzene-1-sulfonyl chlorideHCID 595783904-(5-Amino-pyridin-3-yl)-2-chloro-benzonitrile

Product 1

HCID 49819529N-[5-(3-chloro-4-cyano-phenyl)-pyridin-3-yl]-4-ethyl-benzenesulfonamideYield 41.4%

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 4-ethyl-benzenesulfonyl chloride (15.5 μl, 96 μmol, 1.1 eq). The product was purified by precipitation in methanol and lyophilized to give N-[5-(3-chloro-4-cyano-phenyl)-pyridin-3-yl]-4-ethyl-benzenesulfonamide (14.3 mg, >95% purity, yield: 41.4%).

Workup

  1. customThe product was purified by precipitation in methanol

Sources & evidence

ORD record
ord-79606644c21744c19c6327cb89604270
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

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