Methanol → Methyl 2-methyl-1H-pyrrolo[2,3-c]pyridine-3-carboxylate

HRID 1527090Notes

Reaction equation

HRID 1527090 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[C:13]2[C:8](=[CH:9][N:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[CH3:14])=[O:4].[OH-:17].[K+].[CH3:19]O>>[CH3:14][C:6]1[NH:7][C:8]2=[CH:9][N:10]=[CH:11][CH:12]=[C:13]2[C:5]=1[C:3]([O:4][CH3:19])=[O:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 1177789402,2,2-trichloro-1-(2-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)ethanone

Product 1

HCID 89739208Methyl 2-methyl-1H-pyrrolo[2,3-c]pyridine-3-carboxylateYield 83%

Procedure

A mixture of 2,2,2-trichloro-1-(2-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)ethanone (5.24 g, 18.9 mmol) and KOH (1.2 g, 20.9 mmol) in MeOH (100 mL) was stirred at room temperature for 16 hour. The reaction mixture was concentrated to remove MeOH, the residue was partitioned between EA and Water. The organic layer was washed with brine, dried and concentrated to afford methyl 2-methyl-1H-pyrrolo[2,3-c]pyridine-3-carboxylate (3 g, 83%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove MeOH
  3. customthe residue was partitioned between EA and Water
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-164148a598e748d281691f34c43e2a30
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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