Methanol → HCID 90186657, compound

HRID 2201818Notes

Reaction equation

HRID 2201818 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[Cl-].[Al+3].[Cl-].[Cl-].[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17](Cl)=[O:18].CO>ClCCl>[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17]([C:3]1[C:4]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:1][CH:2]=1)=[O:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 92196-AzaindoleHCID 783922,6-Dichlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 90186657HCID 90186657, compoundYield 41.66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1H-Pyrrolo[2,3-c]pyridine (0.5 g, 4.2 mmol) was added to a stirred suspension of aluminium chloride (2.82 g, 21.1 mmol) in dry dichloromethane (100 mL) and the mixture was stirred at room temperature for 1 hour. This was followed by drop-wise addition of 2,6-dichloro benzoyl chloride (4.42 g, 21.1 mmol). The resulting reaction mixture was stirred at room temperature for 8 hours. Methanol (25 mL) was added cautiously to quench the reaction mass followed by concentration under vacuum. The resulting residue was neutralized using aqueous sodium bicarbonate solution followed by partitioning with ethyl acetate (3×100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. Purification by silica gel column chromatography using ethyl acetate and hexane gradient as eluent afforded (2,6-dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone (0.5 g, 41.66%).

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at room temperature for 8 hours
  3. customto quench the reaction mass
  4. concentrationfollowed by concentration under vacuum
  5. customby partitioning with ethyl acetate (3×100 mL)
  6. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-6bffaed4fd3140c5be32cdb4974321ce
Source dataset
uspto-grants-2016_06
Patent number
US09364466B2

Reaction notes

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