4-Fluorobenzenesulfonyl chloride → HCID 49819528, compound

HRID 1897752Notes

Reaction equation

HRID 1897752 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]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1>[Cl:16][C:10]1[CH:9]=[C:8]([C:4]2[CH:3]=[C:2]([NH:1][S:24]([C:21]3[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=3)(=[O:26])=[O:25])[CH:7]=[N:6][CH:5]=2)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13]

Participants

4

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 595783904-(5-Amino-pyridin-3-yl)-2-chloro-benzonitrile

Product 1

HCID 49819528HCID 49819528, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

According to general 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-fluoro-benzenesulfonyl chloride (18.6 mg, 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-fluoro-benzenesulfonamide (13.5 mg, >95% purity, yield: 40%).

Workup

  1. customThe product was purified by precipitation in methanol

Sources & evidence

ORD record
ord-2a0bbaa7e96643b1bdd21dfd5ffaab3f
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

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