Diethyl Ether → 1H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid, methyl ester

HRID 1865180Notes

Reaction equation

HRID 1865180 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13]C)=[O:11].C([O-])([O-])=O.[K+].[K+].CCOCC>CO.O>[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 11579250ethyl 1H-pyrrolo(3,2-b)pyridine-2-carboxylate

Product 1

HCID 222817761H-Pyrrolo[3,2-b]pyridine-2-carboxylic acid, methyl esterYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

Add to ethyl 4-azaindole-2-carboxylate 4a (42.3 mmol) in MeOH (50 mL), K2CO3 (1.20 equiv, 50.7 mmol) and stir the suspension with heating to 55° C. for 1 h. Monitor the reaction by tlc (Et2O/hept). When complete, concentrate the reaction in vacuo, dilute with H2O and stir for 15 min. Collect the solid by filtration and dry in a vacuum oven at 65° C. for 3 h to afford about 90% to about 100% of the desired methyl 4-azaindole-2-carboxylate 5a.

Workup

  1. concentrationWhen complete, concentrate
  2. customthe reaction in vacuo
  3. stirringstir for 15 min
  4. customCollect the solid
  5. filtrationby filtration
  6. customdry in a vacuum oven at 65° C. for 3 h

Sources & evidence

ORD record
ord-fb02245b41184924b43f47cb8f883409
Source dataset
uspto-grants-2009_12
Patent number
US07626027B2

Reaction notes

Loading…