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CAS No. : | 1349151-98-9 | MDL No. : | MFCD16995643 |
Formula : | C14H22BNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MPMZBWLBVFEODR-UHFFFAOYSA-N |
M.W : | 263.14 | Pubchem ID : | 58070386 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With potassium acetate In 1,4-dioxane at 100℃; for 16.25 h; Inert atmosphere | Step 2 : l-Isopropyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2-one[00155] Potassium acetate (10.23 g, 104.2 mmol) and Pd(dppf)Cl2-CH3CN (914.6 mg, 1.250 mmol) were added to a stirred solution of 5-bromo-l-isopropylpyridin-2(lH)-one (9 g, 41.65 mmol) and bis(dipinacolato)diboron (15.87 g, 62.50 mmol) in dioxane (100 mL). The solvent was degassed by bubbling with 2 for 15 minutes then the reaction was heated at 100 °C for 16 hours under an atmosphere of nitrogen. The reaction mixture was diluted with EtOAc and the organic layer washed with water ( x 2) and brine (x 1). The organic layer was dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion.(TM)., 330 g column, eluting with 5 to 60percent EtOAc/DCM) to give the sub-title product as a light orange solid (7.9 g, 72percent Yield). XH NMR (400.0 MHz, CDCI3) δ 1.31 (s, 12H), 1.39 (d, 6H), 5.26 (hept, IH), 6.52 (d, IH), 7.56 (dd, IH) and 7.78 (s, IH) ppm; MS (ES+) 264.3. |
72% | With potassium acetate In 1,4-dioxane at 100℃; for 16 h; Inert atmosphere | [00172] Step 2: 5-Bromo-l-isopropyl-pyridin-2-one (9.0 g, 41.7 mmol),bis(dipinacolato)diboron (15.9 g, 62.5 mmol) , potassium acetate (10.2 g, 104.2 mmol) and Pd(dppf)Ci2 (915 mg, 1.25 mmol) were suspended in dioxane (30 mL). The reaction mixture was degassed then heated at 100 °C under an atmosphere of nitrogen for 16 h. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous Na2S04, filtered, and concentrated in vacuo. Silica gel chromatography (5-60percent ethyl acetate/dichloromethane) provided l-isopropyl-5-(4,4,5,5-tetramethyl- 1,3,2 -dioxaborolan-2- yl)pyridin-2(lH)-one (7.9 g, 72percent yield). LC/MS m/z 264.3 [M+H]+. XH NMR (400 MHz, CDCI3) δ 7.78 (s, 1H), 7.56 (dd, J= 9.0, 1.7 Hz, 1H), 6.52 (d, J= 9.1 Hz, 1H), 5.26 (hept, J= 6.9 Hz, 1H), 1.39 (d, J= 6.9 Hz, 6H), 1.31 (s, 12H). |
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