Methanol → (6-Chloro-pyridin-3-yl)-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 550953Notes

Reaction equation

HRID 550953 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[NH:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]=[CH:6]1.[Cl:14][C:15]1[N:20]=[CH:19][C:18]([C:21](Cl)=[O:22])=[CH:17][CH:16]=1.CO>C(Cl)Cl>[Cl:14][C:15]1[N:20]=[CH:19][C:18]([C:21]([C:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:5][CH:6]=2)=[O:22])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 27821656-Chloronicotinoyl ChlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 57588066(6-Chloro-pyridin-3-yl)-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methanoneYield 89.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Into a round bottom flask was added aluminum trichloride (16.0 g, 0.12 mol) and methylene chloride (100.0 mL) under an atmosphere of nitrogen. Into the reaction mixture, was added 1H-Pyrrolo[2,3-b]pyridine 1 (3.2 g, 0.027 mol) in methylene dichloride (20.0 mL). The reaction was stirred at room temperature for 70.0 minutes, and then 6-Chloropyridine-3-carbonyl chloride 8 (5.4 g, 0.031 mol) in methylene chloride (10.0 mL) was added. The reaction mixture was stirred at room temperature for 3 hours. Methanol (10 mL) was added to the reaction mixture and the solvent was evaporated in vacuo. The residue was poured into water, and the precipitated product was removed by filtration. The aqueous layer was extracted with ethyl acetate, and then the organic layer was dried and concentrated and combined with the solid isolated by filtration to give 7 (6.2 g, yield 88.6%) as a white solid (M+1=258).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. customthe solvent was evaporated in vacuo
  3. additionThe residue was poured into water
  4. customthe precipitated product was removed by filtration
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. customthe organic layer was dried
  7. concentrationconcentrated
  8. customisolated by filtration

Sources & evidence

ORD record
ord-33ca973a5cf14f6c83aa047d9fb1a304
Source dataset
uspto-grants-2011_05
Patent number
US07947708B2

Reaction notes

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