4-Fluoro-2-methylbenzenesulfonyl chloride → N-[5-(3-chloro-4-cyano-phenyl)-pyridin-3-yl]-4-fluoro-2-methyl-benzenesulfonamide

HRID 1897756Notes

Reaction equation

HRID 1897756 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])=[C:20]([CH3:28])[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][C:20]=3[CH3:28])(=[O:25])=[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 27786024-Fluoro-2-methylbenzenesulfonyl chlorideHCID 595783904-(5-Amino-pyridin-3-yl)-2-chloro-benzonitrile

Product 1

HCID 49819663N-[5-(3-chloro-4-cyano-phenyl)-pyridin-3-yl]-4-fluoro-2-methyl-benzenesulfonamideYield 48.7%

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-fluoro-2-methyl-benzenesulfonyl chloride (14 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-fluoro-2-methyl-benzenesulfonamide (17 mg, >95% purity, yield: 48.7%).

Workup

  1. customThe product was purified by precipitation in methanol

Sources & evidence

ORD record
ord-f266f4f563324fe2a2f2c544d4a61496
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

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