2,4-Dimethylpyrrole → (2-chloro-pyridin-3-yl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methanone

HRID 456614Notes

Reaction equation

HRID 456614 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:15][C:16]1[NH:17][CH:18]=[C:19]([CH3:21])[CH:20]=1>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([C:4]([C:18]2[NH:17][C:16]([CH3:15])=[CH:20][C:19]=2[CH3:21])=[O:5])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

6

Reactant 3

HCID 395392,4-DimethylpyrroleHCID 27745412-Chloronicotinoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18436871(2-chloro-pyridin-3-yl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methanoneYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Chloronicotinoyl chloride (3.4 g, 20 mmol) (Aldrich, Milwaukee, Wis.) was added to a solution of aluminum chloride (2.7 g, 20 mmol) (Aldrich, Milwaukee, Wis.) in dichloromethane (100 mL) at 0° C., followed by a solution of 2,4-dimethylpyrrole (2.9 g, 30 mmol) in dichloromethane (20 mL). The mixture was then stirred at room temperature for one hour. The reaction was diluted with ethyl acetate, washed with brine, dried and concentrated. The residue was purified on a silica gel column to give 2.9 g (62%) of (2-chloro-pyridin-3-yl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methanone.

Workup

  1. washwashed with brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-f128c7020f274fdc9da5b4fe9232538e
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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