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

HRID 456628Notes

Reaction equation

HRID 456628 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Cl:6][C:7]1[N:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:8]=1[C:9](Cl)=[O:10]>C(Cl)Cl.O.[Ti](Cl)(Cl)(Cl)Cl>[Cl:6][C:7]1[C:8]([C:9]([C:2]2[NH:1][CH:5]=[CH:4][CH:3]=2)=[O:10])=[CH:12][CH:13]=[C:14]([Cl:16])[N:15]=1.[Cl:6][C:7]1[C:8]([C:9]([C:3]2[CH:4]=[CH:5][NH:1][CH:2]=2)=[O:10])=[CH:12][CH:13]=[C:14]([Cl:16])[N:15]=1

Participants

7

Reactant 2

HCID 8027PyrroleHCID 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 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Titanium (IV) chloride 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-6bce0ec7330841a09d18628e21fe18f2
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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