Acetyl chloride → 1-(6-Methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

HRID 922440Notes

Reaction equation

HRID 922440 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:15](Cl)(=[O:17])[CH3:16].C(=O)([O-])O.[Na+]>ClC(Cl)C>[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[C:10]([C:15](=[O:17])[CH3:16])[C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 114577166-Methyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 683086561-(6-Methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 6-methyl-1H-pyrrolo[2,3-b]pyridine (500 mg) in dichloroethane (6 mL) were added aluminum chloride (1.09 g) and acetyl chloride (0.40 mL), and then the mixture was stirred at room temperature for 1.5 hours. The reaction solution was poured into aqueous saturated sodium hydrogen carbonate solution, and extracted with chloroform. The organic layer was washed with saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was triturated with isopropyl ether to 1-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone [REx(8-1)] (481 mg) as a yellow powder.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was triturated with isopropyl ether to 1-(6-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone [REx(8-1)] (481 mg) as a yellow powder

Sources & evidence

ORD record
ord-b6a6fd5c48e14501bfbf662271d3427f
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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