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Chemical Structure| 910235-65-3 Chemical Structure| 910235-65-3

Structure of 910235-65-3

Chemical Structure| 910235-65-3

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Product Details of [ 910235-65-3 ]

CAS No. :910235-65-3
Formula : C24H32BNO3
M.W : 393.33
SMILES Code : O=C(NC1=CC=CC(B2OC(C)(C)C(C)(C)O2)=C1C)C3=CC=C(C(C)(C)C)C=C3
MDL No. :MFCD22570803

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Application In Synthesis of [ 910235-65-3 ]

* 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.

  • Downstream synthetic route of [ 910235-65-3 ]

[ 910235-65-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 910543-72-5 ]
  • [ 910235-65-3 ]
  • [ 1011797-06-0 ]
YieldReaction ConditionsOperation in experiment
72% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 170℃; for 0.5h;Microwave irradiation; A mixture of 46 (0.248 g, 1.22 mmol, CASRN 910543-72-5), A-6 (0.574 g, 1.46 mmol), Na2CO3 (0.388 g, 3.66 mmol), and Pd(0)(PPh3)4 (0.141 g, 0.122 mmol) in DME (10 mL) and H2O (5 mL) was stirred and heated at 170 C. for 30 min in a microwave synthesizer. The mixture was partitioned between EtOAc (100 mL) and H2O (100 mL). The aqueous layer was extracted with two 100 mL portions of EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated. The crude product was purified by SiO2 chromatography eluting with a MeOH/DCM gradient (0 to 4% MeOH) to afford 0.341 g (72%) of 48 as a yellow solid. The material was not completely pure but was used as is in the next step.
68% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 95℃; for 16.25h; N-[3-(5-Amino-l-methyl-6-oxo-l,6-dihydro-pyridin-3-yl)-2-methyl-phenyl]-4- terf-butyl-benzamide (5); <n="68"/>[00187] A 48-mL sealed tube equipped with a magnetic stirring bar was charged with 3-amino-5-bromo-l -methyl- lH-pyridin-2-one (4) (0.10 g, 0.50 mmol), 4-tert-butyl-iV-[2-methyl-3-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]- benzamide (0.24 g, 0.70 mmol), and Pd(PPh3)4 (0.030 g, 0.025 mmol) in DME (10 mL) and IN Na2CO3 (5 mL). After the mixture was degassed for 15 min., it was heated at 95 0C for 16 h. Then, the reaction mixture was cooled to room temperature and poured into H2O (10 mL). To this was added dichloromethane and the phases were separated. The aqueous layer was extracted with dichloromethane, and the combined organic layers were washed with H2O (5 mL) and brine (5 mL), dried (Na2SO4), and concentrated. The crude mixture was purified by column chromatography, gradient 0-10 % MeOH in dichloromethane/ether (1/1), to afford 0.14 g (68 %) of iV-[3-(5-amino-l-methyl-6-oxo-l,6-dihydro-pyridin-3-yl)-2-methyl- phenyl]-4-te/t-butyl-benzamide (5) as a solid.
68% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 95℃; for 16h; N-[3-(5-Amino-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide (3) A 48-mL seal tube equipped with a magnetic stirring bar was charged with <strong>[910543-72-5]3-amino-5-bromo-1-methyl-1H-pyridin-2-one</strong> (2) (0.10 g, 0.50 mmol), 4-tert-butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (0.24 g, 0.70 mmol), and Pd(PPh3)4 (0.030 g, 0.025 mmol) in DME (10 mL) and 1N Na2CO3 (5 mL). After the mixture was degassed for 15 min., it was heated at 95 C. for 16 h. Then, the reaction mixture was cooled to room temperature and poured into H2O (10 mL). To this was added dichloromethane and the phases were separated. The aqueous layer was extracted with dichloromethane, and the combined organic layers were washed with H2O (5 mL) and brine (5 mL), dried (Na2SO4), and concentrated. The crude mixture was purified by column chromatography, gradient 0-10% MeOH in dichloromethane/ether (1/1), to afford 0.14 g (68%) of N-[3-(5-amino-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-2-methyl-phenyl]-4-tert-butyl-benzamide (3) as a solid.
 

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