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Pyrrole → (2,6-dichloro-pyridin-3-yl)-(1H-pyrrol-2-yl)-methanone

HRID 456626
Notes
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Reaction equation

HRID 456626 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[NH:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[Cl:11][C:12]1[N:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15]>C(Cl)Cl.O>[Cl:11][C:12]1[C:13]([C:14]([C:7]2[NH:6][CH:10]=[CH:9][CH:8]=2)=[O:15])=[CH:17][CH:18]=[C:19]([Cl:21])[N:20]=1.[Cl:11][C:12]1[C:13]([C:14]([C:8]2[CH:9]=[CH:10][NH:6][CH:7]=2)=[O:15])=[CH:17][CH:18]=[C:19]([Cl:21])[N:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8027PyrroleHCID 24287Tin tetrachlorideHCID 122639842,6-Dichlorpyridine-3-carbonyl chloride

Product 2

HCID 18436867(2,6-dichloro-pyridin-3-yl)-(1H-pyrrol-2-yl)-methanoneHCID 18436868(2,6-dichloro-pyridin-3-yl)-(1H-pyrrol-3-yl)-methanone

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent2×

Procedure

Tin (IV) chloride (Aldrich, Milwaukee, Wis.) in DCM (10 mL) was added dropwise to a mixture of pyrrole (4 g) and 2,6-dichloro-nicotinoyl chloride (6 g) in DCM (150 mL) at 0° C. The mixture was then stirred at room temperature for 30 mins. The reaction was diluted with water, washed with water (200 mL), 2N NaOH (50 mL) and brine, dried and concentrated. The residue was purified on a silica gel column to give 1.8 g of (2,6-dichloro-pyridin-3-yl)-(1H-pyrrol-2-yl)-methanone and 380 mg of (2,6-dichloro-pyridin-3-yl)-(1H-pyrrol-3-yl)-methanone.

Workup

  1. washwashed with water (200 mL), 2N NaOH (50 mL) and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-67f6d6cc558645839b85f8196f4bbcbe
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07186716B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes