3-(Methylsulfonyl)benzenesulfonyl chloride → N-[2-(4,5-Dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-3-(methylsulfonyl)-N-{[3-(methylsulfonyl)phenyl]sulfonyl}benzenesulfonamide

HRID 1851576Notes

Reaction equation

HRID 1851576 reaction equation
[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:15].[CH3:16][S:17]([C:20]1[CH:21]=[C:22]([S:26](Cl)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)(=[O:19])=[O:18]>N1C=CC=CC=1>[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[N:15]([S:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([S:17]([CH3:16])(=[O:19])=[O:18])[CH:21]=1)(=[O:28])=[O:27])[S:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([S:17]([CH3:16])(=[O:19])=[O:18])[CH:21]=1)(=[O:28])=[O:27]

Participants

4

Reactant 2

HCID 2203303-(Methylsulfonyl)benzenesulfonyl chlorideHCID 579017772-(4,5-Dihydro-1,3-thiazol-2-yl)-1H-indole-7-amine

Product 1

HCID 57901851N-[2-(4,5-Dihydro-1,3-thiazol-2-yl)-1H-indol-7-yl]-3-(methylsulfonyl)-N-{[3-(methylsulfonyl)phenyl]sulfonyl}benzenesulfonamideYield 22.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indole-7-amine (100 mg) and pyridine (3 mL) was added 3-(methylsulfonyl)benzenesulfonyl chloride (140 mg) at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound (41 mg, yield 14%) as pale-yellow crystals. M+1=654.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-1164e083b1794fd6954564e7272937a8
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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