2-Thiophenesulfonyl chloride → HCID 136060822, compound

HRID 1851556Notes

Reaction equation

HRID 1851556 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[NH2:17])[S:5][C:6]=1[CH3:7].[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[S:23](Cl)(=[O:25])=[O:24]>N1C=CC=CC=1>[CH3:1][C:2]1[N:3]=[C:4]([C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][C:11]=3[NH:17][S:23]([C:19]2[S:18][CH:22]=[CH:21][CH:20]=2)(=[O:25])=[O:24])[S:5][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 136060833HCID 136060833, compound

Product 1

HCID 136060822HCID 136060822, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 2-(4,5-dimethyl-1,3-thiazol-2-yl)-1H-indole-7-amine (0.10 g) and pyridine (8 mL) was added thiophene-2-sulfonyl chloride (0.090 g) at 4° C., and the mixture was stirred at room temperature for 15 hr. The reaction solution was concentrated. The obtained residue was diluted with ethyl acetate, washed with aqueous citric acid solution and saturated brine, dried over-anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate) to give the title compound (142 mg, yield 89%) as pale-purple crystals. melting point 210-211° C.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionThe obtained residue was diluted with ethyl acetate
  3. washwashed with aqueous citric acid solution and saturated brine, dried over-anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f6f328e3ae6041b98dc2dee5f8a59aba
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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