8-methoxy-2-methylbenzofuro[2,3-b]pyridine synthesis
- Product Name:8-methoxy-2-methylbenzofuro[2,3-b]pyridine
- CAS Number:1609373-96-7
- Molecular formula:C13H11NO2
- Molecular Weight:213.23
1609373-95-6
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Yield:1609373-96-7 60.4%
Reaction Conditions:
with tert.-butylnitrite;acetic acid in tetrahydrofuran at 0; for 2 h;
Steps:
Preparation of 8-methoxy-2-methylbenzofuro[2,3-b]pyridine:
Into a solution of 3-(2,3-dimethoxyphenyl)-6-methylpyridin-2-amine (14.5 g, 59.4 mmol) in acetic acid (200 ml)and THF (67 ml) was added dropwise tert-butylnitrite (14.1 ml, 106.9 mmol) at 0 °C. After stirring at this temperature for2 h, the reaction mixture was allowed to warm to room temperature. Upon evaporation off the solvent, the residue waspartitioned between ethyl acetate and water. The organic phas was isolated, washed with aqueous sodium bicarbonateand brine, dried over sodium sulfate. Unpon evaporation off the solvent, the residue was purified by column chromatographyon silica gel with 25% ethyl acetate in hexane to obtain 7.65 g (60.4%) of desired product as a pale yellow solid.
References:
EP2730583,2014,A1 Location in patent:Paragraph 0151; 0152
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