1-Phenylsulfonylpyrrole → (1-benzenesulfonyl-1H-pyrrol-2-yl)-(2-chloro-pyridin-3-yl)-methanone

HRID 456678Notes

Reaction equation

HRID 456678 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[C:11]1([S:17]([N:20]2[CH:24]=[CH:23][CH:22]=[CH:21]2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C.C(OCC)(=O)C>[C:11]1([S:17]([N:20]2[CH:21]=[CH:22][CH:23]=[C:24]2[C:4]([C:3]2[C:2]([Cl:1])=[N:10][CH:9]=[CH:8][CH:7]=2)=[O:5])(=[O:19])=[O:18])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 1401461-PhenylsulfonylpyrroleHCID 27745412-Chloronicotinoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18436866(1-benzenesulfonyl-1H-pyrrol-2-yl)-(2-chloro-pyridin-3-yl)-methanoneYield 49%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-nicotinoyl chloride (1.17 g) (Aldrich, Milwaukee, Wis.) and 1-benzensulfonyl-1H-pyrrole (1 g) (Aldrich) in dichloroethane (15 mL) was added aluminum chloride (1.1 g). After stirring at room temperature for one hour, the reaction was diluted with ethyl acetate, washed with water, base and brine, dried and purified to give 820 mg of (1-benzenesulfonyl-1H-pyrrol-2-yl)-(2-chloro-pyridin-3-yl)-methanone.

Workup

  1. washwashed with water, base and brine
  2. customdried
  3. custompurified

Sources & evidence

ORD record
ord-1f863861b2064232986436d29801d7a3
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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