Methanol → methyl 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

HRID 2170994Notes

Reaction equation

HRID 2170994 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[NH:10][C:5]2=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:19]O>>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:11]([O:13][CH3:19])=[O:12])[NH:10][C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 116655855-chloro-1H-pyrrolo(3,2-b)pyridine-2-carboxylic acid

Product 1

HCID 84677991methyl 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylateYield 59.8%

Procedure

5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid 11-b (25.20 g, 128.18 mmol) was added to a refluxing mixture of sulfuric acid (20 ml) and methanol (400 ml). The mixture was refluxed overnight. The mixture was then evaporated and a cold NaHCO3 solution was added until basic pH. The precipitate was filtered off and dried, yielding 16.15 g of the desired product (59.8%). m/z=211.17 (M+H)+, Cl pattern.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe mixture was then evaporated
  3. additiona cold NaHCO3 solution was added until basic pH
  4. filtrationThe precipitate was filtered off
  5. customdried

Sources & evidence

ORD record
ord-42f1d963ce274f7582acc92a900f9933
Source dataset
uspto-grants-2015_06
Patent number
US09051317B2

Reaction notes

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