(5-(prop-1-yn-1-yl)pyridin-3-yl)boronic acid synthesis
- Product Name:(5-(prop-1-yn-1-yl)pyridin-3-yl)boronic acid
- CAS Number:1231934-45-4
- Molecular formula:C14H18BNO2
- Molecular Weight:243.11
917772-69-1
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Yield:1231934-45-4 508 mg
Reaction Conditions:
with tetrakis(triphenylphosphine) palladium(0);potassium acetate in 1,4-dioxane at 110; for 2.5 h;Inert atmosphere;
Steps:
4.2 Step 2
Step 2 [0254] Compound (28) (500 mg), diboron pinacol ester (1.17 g), potassium acetate (751 mg) and a palladium(0)tetrakistriphenylphosphine complex (295 mg) were put into an eggplant flask. After being purged with nitrogen gas, dioxane (20 ml) was added and stirred at 110° C. for 2.5 hours. The reaction solution was cooled to room temperature and made acidic using water and a 2 mol/L aqueous hydrochloric acid solution. The impurity was removed by back-extraction with ethyl acetate. The aqueous layer was made alkaline using sodium hydroxide and the product was extracted to the organic layer with ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure to afford Compound (29) (508 mg). [0255] 1H-NMR (CDCl3) δ: 1.34 (s, 12H), 2.06 (s, 3H), 8.06 (dd, J=2.2, 1.7 Hz, 1H), 8.66 (d, J=2.2 Hz, 1H), 8.79 (d, J=1.7 Hz, 1H).
References:
US2013/210839,2013,A1 Location in patent:Paragraph 0254; 0255
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