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

HRID 2206602Notes

Reaction equation

HRID 2206602 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-4ca2dc4e16704040bcf7136dc9f28b98
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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