Tetrabutylammonium Fluoride → methyl 1H-pyrrolo[2,3-b]pyridine-5-carboxylate
Reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8](C#C[Si](C)(C)C)[C:7]([NH:16][C:17](=O)[CH3:18])=[N:6][CH:5]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]2[CH:18]=[CH:17][NH:16][C:7]2=[N:6][CH:5]=1)=[O:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of 6-acetylamino-5-trimethylsilanylethynyl-nicotinic acid methyl ester (24.4 mmol theoretical from previous step) in tetrahydrofuran (15 mL) was added tetrabutylammonium fluoride (1 M solution in tetrahydrofuran, 100 mL, 100 mmol) at 25° C. The mixture was heated at reflux at 80° C. for 2 h and then cooled to 25° C. The resulting mixture was extracted with ethyl acetate, washed with brine and dried over sodium sulfate. The solvent was evaporated in vacuo to afford 1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (3.4 g, 79% over two steps) as a light yellow solid: 1H NMR (400 MHz, CDCl3) δ ppm 4.01 (s, 3H), 6.71 (d, J=3.6 Hz, 1H), 7.53 (d, J=3.6 Hz, 1H), 8.77 (s, 1H), 9.04 (s, 1H).
Workup
- temperatureThe mixture was heated
- temperaturecooled to 25° C
- extractionThe resulting mixture was extracted with ethyl acetate
- washwashed with brine
- dry with materialdried over sodium sulfate
- customThe solvent was evaporated in vacuo
Sources & evidence
- ORD record
- ord-7dd3697937274074b317a28298b05e43
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08222416B2
Reaction notes
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