2-Chloropyridine-3-sulfonyl chloride → 2-chloro-N-methyl-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]pyridine-3-sulfonamide

HRID 1851619Notes

Reaction equation

HRID 1851619 reaction equation
Cl.[CH3:2][NH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)=[CH:9]2.[Cl:18][C:19]1[C:24]([S:25](Cl)(=[O:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=1>N1C=CC=CC=1>[Cl:18][C:19]1[C:24]([S:25]([N:3]([CH3:2])[C:4]2[CH:5]=[CH:6][CH:7]=[C:8]3[C:12]=2[NH:11][C:10]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[CH:9]3)(=[O:27])=[O:26])=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 102199682-Chloropyridine-3-sulfonyl chlorideHCID 67109280N-Methyl-2-(1,3-thiazol-2-yl)-1H-indole-7-amine hydrochloride

Product 1

HCID 579016132-chloro-N-methyl-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]pyridine-3-sulfonamideYield 62.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-methyl-2-(1,3-thiazol-2-yl)-1H-indole-7-amine monohydrochloride (132 mg) in pyridine (3 mL) was added 2-chloropyridine-3-sulfonyl chloride (120 mg) at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound (126 mg, yield 62%) as pale-yellow crystals. melting point 203° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-229858f0c42a48599ced0a2b7a1ebfb6
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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