3-Chloro-2-isobutoxypyridine-5-boronic acid pinacol ester synthesis
- Product Name:3-Chloro-2-isobutoxypyridine-5-boronic acid pinacol ester
- CAS Number:1387634-81-2
- Molecular formula:C15H23BClNO3
- Molecular Weight:311.61
1289093-31-7
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1387634-81-2
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Yield:1387634-81-2 95%
Reaction Conditions:
with bis-triphenylphosphine-palladium(II) chloride;potassium acetate in 1,4-dioxane; for 4 h;Reflux;
Steps:
12 PREPARATION 12 Synthesis of 3-chloro-2-isobutoxy-5-(4,4,5,5-tetramethyl- -dioxaborolan-2-yl)pyridine
A mixture of 5-bromo-3-chloro-2-isobutoxypyridine (Preparation 1 1, 10.6 g, 40.0 mmol), borane pinacol ester (12.7 g, 50.0 mmol), dichlorobistriphenylphosphine palladium (Π) (2.80 g, 4.00 mmol) and potassium acetate (11.8 g, 120 mmol) in dioxane was refluxed for 4 h. The reaction mixture was cooled to ambient temperature and then diluted with ethyl acetate (300 mL), washed with brine (3 x 100 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified via silica gel column chromatography eluting with ethyl acetate in hexanes using 10-30% gradient to afford the title compound as a colourless liquid which was used in the next step without further characterization (1 1.9 g, 95% yield): MS (ES+) 312.2, 314.2 (M + 1).
References:
WO2014/8458,2014,A2 Location in patent:Paragraph 0314-0315
1289093-31-7
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73183-34-3
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1387634-81-2
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1387634-81-2
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1387634-81-2
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2402-77-9
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1387634-81-2
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