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Chemical Structure| 832114-00-8 Chemical Structure| 832114-00-8
Chemical Structure| 832114-00-8

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CAS No.: 832114-00-8

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Product Details of 3,5-Dimethylisoxazole-4-boronic acid pinacol ester

CAS No. :832114-00-8
Formula : C11H18BNO3
M.W : 223.08
SMILES Code : CC1(C)C(C)(C)OB(C2=C(C)ON=C2C)O1
MDL No. :MFCD05863910
InChI Key :CVLHETBAROWASE-UHFFFAOYSA-N
Pubchem ID :2758656

Safety of 3,5-Dimethylisoxazole-4-boronic acid pinacol ester

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 3,5-Dimethylisoxazole-4-boronic acid pinacol ester

* 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 [ 832114-00-8 ]

[ 832114-00-8 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 832114-00-8 ]
  • [ 1613695-14-9 ]
  • 2
  • [ 832114-00-8 ]
  • [ 6127-19-1 ]
  • [ 1613695-40-1 ]
  • 3
  • [ 832114-00-8 ]
  • [ 540516-28-7 ]
  • [ 1613695-43-4 ]
  • 4
  • [ 832114-00-8 ]
  • [ 214915-72-7 ]
  • [ 1613695-49-0 ]
  • 5
  • [ 1741-50-0 ]
  • [ 832114-00-8 ]
  • [ 1613695-61-6 ]
  • 6
  • [ 832114-00-8 ]
  • [ 2604-39-9 ]
  • C10H10N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
> 99% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere; To a solution of 58 (1.00 g, 5.76 mmol) in 1,4-dioxane (40 mL) and water (4 mL) was added 3,5-dirnethyl-4-(4,4,5,5-tetrarrethy -l,3/2--dioxaboroian-2-yi)isoxazoe (1.93 g, 8.64 mmol), potassium carbonate (1.59 g, 11.5 mmol), and tetrakis(triphenylphosphine)pailadium(0) (333 mg, 0.288 mmol). The reaction mixture was purged with nitrogen and heated at 90 °C overnight. The reaction mixture was cooled to room temperature, concentrated and purified bychromatography (silica gel, 0-100percent ethyl acetate in hexanes) to afford 59 (1.42 g, >99percent) as a yellow solid: H N (300 MHz, CDCI3) delta 9.26 (s, 1H), 6.67 (s, 1H), 6.90-6.00 (bs, 2H), 2.61 (s, 3H), 2.44 (s, 3H); ESI m/z 235 IM + H]+.
  • 7
  • [ 832114-00-8 ]
  • [ 3430-29-3 ]
  • C11H12BrN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 80℃; for 16h;Inert atmosphere; To a solution of 77 (4.4 g, 16,5 rnmoi) in 1,4-dioxane (100 rnL) was added 3,5-dimethy-4-(4,4,5,5-tetramethyi-l,3,2-dioxaborolan-2-yl)isoxazoe (4.4 g, 19.8 mmol), Na2C03(2.0 M in H?0, 25 mL, 50.0 mmol} and tetrakis(triphenyphosphine)paiadium(0) (959 mg, 0.83 mmol). The reaction mixture was purged with nitrogen and heated at 80 "C for 16 h. The mixture was diluted with EtOAc (100 mL) and washed with brine (50 mL). The organic ayer was dried over NazS04, and filtered. The fitrate was concentrated and then purified by chromatography (silica gel, 0-60% ethyi acetate/hexanes) to afford 78 (2.64 g, 57%) as an off-white solid: H N R (300 MHz, DMSO-d6) delta 7.71 (s, 1H), 6.32 (s, 2H), 2.22 (s, 3H), 2.08 (s, 3H), 2.02 (s, 3H).
  • 8
  • [ 832114-00-8 ]
  • [ 118289-17-1 ]
  • C11H10N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 80℃; for 24h;Inert atmosphere; General procedure: To a mixture of 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole (0.50 g, 2.2 mmol), 3-bromobenzaldehyde (0.50 g, 2.7 mmol), Pd(PPh3)4 (0.13 g,0.12 mmol) and sodium carbonate (0.71 g, 6.7 mmol) in toluene/ethanol/H2O (10 mL, 3/1/3) was refluxed under nitrogen atmosphere for 24 h. Then the mixture was diluted with saturatedammonium chloride solution and EtOAc, and the insoluble materialwas filtered through Celite. The organic layer of the filtrate waswashed with water (30 mL) and brine (30 mL), dried over Na2SO4,and evaporated in vacuo. The residue was purified by columnchromatography (EtOAc/petroleum ether, 1/15 to 1/5) to give 7a(0.37 g, 77percent) as a white solid.
  • 9
  • [ 832114-00-8 ]
  • [ 131747-63-2 ]
  • C11H10N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 80℃; for 24h;Inert atmosphere; General procedure: To a mixture of 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole (0.50 g, 2.2 mmol), 3-bromobenzaldehyde (0.50 g, 2.7 mmol), Pd(PPh3)4 (0.13 g,0.12 mmol) and sodium carbonate (0.71 g, 6.7 mmol) in toluene/ethanol/H2O (10 mL, 3/1/3) was refluxed under nitrogen atmosphere for 24 h. Then the mixture was diluted with saturatedammonium chloride solution and EtOAc, and the insoluble materialwas filtered through Celite. The organic layer of the filtrate waswashed with water (30 mL) and brine (30 mL), dried over Na2SO4,and evaporated in vacuo. The residue was purified by columnchromatography (EtOAc/petroleum ether, 1/15 to 1/5) to give 7a(0.37 g, 77percent) as a white solid.
  • 10
  • [ 832114-00-8 ]
  • [ 848366-28-9 ]
  • N-(5-(3,5-dimethylisoxazol-4-yl)-2-methoxypyridin-3-yl)-3,5-dimethylisoxazol-4-amine [ No CAS ]
  • 11
  • [ 832114-00-8 ]
  • [ 848366-28-9 ]
  • C11H11ClN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 90℃; for 16.0h;Inert atmosphere; [0153] To a solution of <strong>[848366-28-9]5-bromo-3-chloro-2-methoxypyridine</strong> (5.0 g, 22.5 mmol), and 3,5-dimethylisoxazole-4-boronic acid pinacol ester (6.0 g, 27.0 mmol) in 1,4-dioxane (188 mL) and water (19 mL) was added potassium carbonate (6.2 g, 44.9 mmol). The mixture was purged with nitrogen for 10 min, and tetrakis(triphenylphosphine)palladium(0) was added (1.3 g, 1.12 mmoi). The mixture was heated to 90 C for 16 h, then diluted with ethyl acetate (100 mL) and washed with brine (100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (silica gel, 0- 30% ethyl acetate/hexanes) to afford 4 as a white solid (4.2 g, 78%): JH NMR (300 MHz, DMSO-d6) delta 8.18 (d, J = 2.1 Hz, 1H), 8.01 (d, J - 2.1 Hz, 1H), 3.99 (s, 3H), 2.40 (s, 3H), 2.22 (s, 3H); ESI m/z 239 [M + H]+.
  • 12
  • [ 832114-00-8 ]
  • [ 89415-54-3 ]
  • C11H14N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 16h;Inert atmosphere; [0161] To a solution of 11 (202 mg, 1.0 mmol) in dioxane (10 mL) was added 3,5- dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole (335 mg, 1.5 mmoi), sodium carbonate (2.0 M in H20, 1.0 mL, 2.0 mmol) and tetrakis(triphenylphosphine)palladium (58 mg, 0.05 mmol). The reaction mixture was purged with nitrogen and was heated at 90 C for 16 h. The mixture was diluted with CH2CI2 (100 mL) and washed with brine (2 * 30 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica gel, 50-100% ethyl acetate/hexanes) afforded 12 (154 mg, 71%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) delta 7.37 (d, J = 1.8 Hz, 1H), 6.66 (d, J = 2.1 Hz, 1H), 5.70 (q, J = 4.5 Hz, 1H), 4.78 (s, 2H), 2.86 (d, J = 4.8 Hz, 3H), 2.34 (s, 3H), 2.17 (s, 3H).
 

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