2-Methoxy-5-(prop-2-en-1-yl)pyridine synthesis
- Product Name:2-Methoxy-5-(prop-2-en-1-yl)pyridine
- CAS Number:1197831-20-1
- Molecular formula:C9H11NO
- Molecular Weight:149.19
13472-85-0
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Yield:1197831-20-1 90%
Reaction Conditions:
with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium phosphate in 1,4-dioxane;water at 100; for 2 h;Inert atmosphere;
Steps:
Step 1: 5-allyl-2-methoxypyridine
To a solution of 5-bromo-2-methoxypyridine (4.2 g, 22.3 mmol) and 2-allyl-4, 4,5,5- tetramethyl-l,3,2-dioxaborolane (5.63 g, 33.5 mmol) in 1,4-dioxane (42 mL) and water (8.4 mL) were added K3PO4 (14.23 g, 67.0 mmol), Pd(dppf)C12 (1.63 g, 2.23 mmol) under N2 atmosphere and the mixture was degassed under N2 atmosphere for three times and stirred under N2 atmosphere at 100 °C for 2 hrs. The mixture was diluted EtOAc (50 mL), washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated to dryness. The residue was purified by flash chromatography (eluted with PE: EtOAc = 50: 1 to 10: 1) to give the title compound (3 g, 90% yield) as light yellow oil. LC/MS (ESI) m/z: 150 (M+H)+.
References:
WO2022/34568,2022,A1 Location in patent:Paragraph 0192
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$8.00/1g
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