Sodium Chloride → 1-[5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-one

HRID 472044Notes

Reaction equation

HRID 472044 reaction equation
[CH2:1]([CH:3]([CH2:7][CH3:8])[C:4](Cl)=[O:5])[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[C:21]1[CH:22]=[C:23]2[CH:29]=[CH:28][NH:27][C:24]2=[CH:25][N:26]=1.[Na+].[Cl-]>C(Cl)Cl>[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[C:21]1[CH:22]=[C:23]2[C:29]([C:4](=[O:5])[CH:3]([CH2:7][CH3:8])[CH2:1][CH3:2])=[CH:28][NH:27][C:24]2=[CH:25][N:26]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 759542-Ethylbutyryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 671524405-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 671525261-[5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Ethyl-butyryl chloride (0.799 mL, 5.8 mmol) is added to a suspension of AlCl3 (770 mg, 5.8 mmol) in DCM (20 mL) at −10° C. The resultant solution is stirred for 15 min at the same temperature, and 5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridine (0.5 g, 2.2 mmol) is added as a solution in DCM (3 mL). The mixture is stirred for 18 h at room temperature. A saturated aqueous NaCl solution (30 mL) is carefully added to the mixture, and stirring is continued for 2 h. Organic layer is separated, and the aqueous solution is extracted with DCM. The combined organic solutions are washed with water and brine, dried (Na2SO4), and concentrated under reduced pressure. Chromatography of the residue on silica gel 10% MeOH-DCM affords 1-[5-(2,6-dimethyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-yl]-2-ethyl-butan-1-one as colorless oil.

Workup

  1. stirringstirring
  2. waitis continued for 2 h
  3. customOrganic layer is separated
  4. extractionthe aqueous solution is extracted with DCM
  5. washThe combined organic solutions are washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b2cfeb843d3041129558f5a283c35e65
Source dataset
uspto-grants-2014_01
Patent number
US08633193B2

Reaction notes

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