Methanol → methyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylate
Reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:19]([OH:21])=[O:20])(=O)=O)C=CC=CC=1.[CH3:22]O>[OH-].[Na+]>[CH3:22][O:21][C:19]([C:11]1[NH:10][C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH:12]=1)=[O:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
0.495 g (1.64 mmol) of 1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid was dissolved in 5 mL of methanol and 3 mL of 2N aqueous sodium hydroxide. The reaction was stirred at 40° C. for 8 h. The solvent was removed under reduced pressure. Residual volatiles were removed by twice codistilling with toluene. The residue was suspended in methanolic hydrochloric acid and stirred for 16 h at RT. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution. The organic phase was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure.
Workup
- customThe solvent was removed under reduced pressure
- customResidual volatiles were removed
- stirringstirred for 16 h at RT
- customThe solvent was removed under reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed with saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
- dry with materialThe organic phase was dried with sodium sulfate
- filtrationfiltered
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-4ead1d055eaf405497792dcc102f083f
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07317027B2
Reaction notes
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