Pyrrole → (2-Chloropyridin-3-yl)(1H-pyrrol-2-yl)methanone

HRID 456616Notes

Reaction equation

HRID 456616 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]([C:4]([C:12]2[NH:11][CH:15]=[CH:14][CH:13]=2)=[O:5])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

6

Reactant 3

HCID 8027PyrroleHCID 27745412-Chloronicotinoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13160528(2-Chloropyridin-3-yl)(1H-pyrrol-2-yl)methanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-chloronicotinoyl chloride (1 eq.) in dichloromethane (10 mL) was added slowly to a mixture of pyrrole (1.5 eq.) (Aldrich, Milwaukee, Wis.) and aluminum chloride (3.5 g, 1 eq.) in dichloromethane (8 mL) at 0° C. The mixture was stirred at 0° C. for 10 mins and at room temperature for 30 mins. The reaction was diluted with ethyl acetate, washed with brine, dried and concentrated. The residue was purified on a silica gel column to give 2.27 g of (2-chloro-pyridin-3-yl)-(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-5133d340ca3f40efb95cb91db39b614c
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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