4-Nitrophenol → 4-(4-Nitrophenoxy)furo[2,3-b]pyridine-2-carboxylic acid methyl ester
Reaction equation
CN1CCCC1=O.C(N(C(C)C)CC)(C)C.[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([O-:19])=[O:18].[CH3:27][O:28][C:29]([C:31]1[O:40][C:34]2=[N:35][CH:36]=[CH:37][C:38](Cl)=[C:33]2[CH:32]=1)=[O:30]>O>[CH3:27][O:28][C:29]([C:31]1[O:40][C:34]2=[N:35][CH:36]=[CH:37][C:38]([O:26][C:23]3[CH:24]=[CH:25][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=3)=[C:33]2[CH:32]=1)=[O:30]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
After adding N-methylpyrrolidone (4.0 ml), diisopropylethylamine (1.3 ml) and para-nitrophenol (822 mg) to 4-chlorofuro[2,3-b]pyridine-2-carboxylic acid methyl ester (1.0 g), the mixture was heated and stirred at 140° C. for 5 hours. After cooling, water was added, extraction was performed with ethyl acetate, the organic layer was washed with water and saturated saline in that order and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. Tetrahydrofuran was used for recrystallization to obtain the title compound (70 mg).
Workup
- temperaturethe mixture was heated
- temperatureAfter cooling
- extractionextraction
- washthe organic layer was washed with water and saturated saline in that order
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customTetrahydrofuran was used for recrystallization
Sources & evidence
- ORD record
- ord-e932449599b64eeea7beccf39108804f
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372981B2
Reaction notes
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