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Organoboron
4-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine
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[ CAS No. 519054-54-7 ] {[proInfo.proName]}

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Chemical Structure| 519054-54-7
Chemical Structure| 519054-54-7
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Product Details of [ 519054-54-7 ]

CAS No. :519054-54-7 MDL No. :MFCD04115377
Formula : C15H22BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :QRAOZQGIUIDZQZ-UHFFFAOYSA-N
M.W : 275.15 Pubchem ID :2795301
Synonyms :

Safety of [ 519054-54-7 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 519054-54-7 ]

* 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 [ 519054-54-7 ]

[ 519054-54-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 519054-54-7 ]
  • [ 1201633-72-8 ]
  • [ 1312412-64-8 ]
YieldReaction ConditionsOperation in experiment
11% With sodium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere; B9 Pd(PPh3)4 (0.03 g, 0.02 mmol) was added to a solution of intermediate 1 (0.2 g, 0.865 mmol), 4-methyl-7-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H- benzo[l,4]oxazine (0.23 g, 0.865 mmol) and Na2C03 (0.23 g, 0.865 mmol) in a mixture of 1 ,2-dimethoxyethane (3 mL) and H20 (lmL) at room temperature. The reaction mixture was stirred at 80°C overnight under a nitrogen atmosphere, then cooled to room temperature and AcOEt (5 mL) added. The organic layer was separated, washed with H20, dried (Na2S04) and the solvent evaporated in vacuo. The residue thus obtained was purified by reverse phase HPLC (gradient elution: 0.1% TFA in ACN/0.1% TFA in H20). The desired fractions were collected, washed with NaHC03 (aqueous saturated solution) and extracted with AcOEt (2 x 100 mL). The combined organic extracts were dried (Na2S04) and evaporated in vacuo affording compound 9 (28 mg, 11% yield).1H NMR (300 MHz, CDCL3) δ ppm 2.09 - 2.22 (m, 2 H), 2.51 - 2.59 (m, H), 2.92 (s, 3 H), 3.00 (t, J=6.1 Hz, 2 H), 3.30 - 3.36 (m, 2 H), 4.20 - 4.25 (m, 2 H), 6.58 (d, J=8.3 Hz, 1 H), 7.34 (d, J=2.3 Hz, 1 H), 7.47 - 7.54 (m, 1 H).
With sodium carbonate In 1,2-dimethoxyethane; water at 20 - 80℃; Inert atmosphere; B.9 Pd(PPh3)4 (0.03 g, 0.02 mmol) was added to a solution of intermediate 1 (0.2 g, 0.865 mmol), 4-methyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[1,4]oxazine (0.23 g, 0.865 mmol) and Na2CO3 (0.23 g, 0.865 mmol) in a mixture of 1,2-dimethoxyethane (3 mL) and H2O (1 mL) at room temperature. The reaction mixture was stirred at 80° C. overnight under a nitrogen atmosphere, then cooled to room temperature and AcOEt (5 mL) added. The organic layer was separated, washed with H2O, dried (Na2SO4) and the solvent evaporated in vacuo. The residue thus obtained was purified by reverse phase HPLC (gradient elution: 0.1% TFA in ACN/0.1% TFA in H2O). The desired fractions were collected, washed with NaHCO3 (aqueous saturated solution) and extracted with AcOEt (2×100 mL). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo affording compound 9 (28 mg, 11% yield). 1H NMR (300 MHz, CDCL3) δ ppm 2.09-2.22 (m, 2H), 2.51-2.59 (m, 2 H), 2.92 (s, 3H), 3.00 (t, J=6.1 Hz, 2H), 3.30-3.36 (m, 2H), 4.20-4.25 (m, 2H), 6.58 (d, J=8.3 Hz, 1H), 7.34 (d, J=2.3 Hz, 1H), 7.47-7.54 (m, 1H).
Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2011/73347, 2011, A1 Location in patent: Page/Page column 42-43
[2]Current Patent Assignee: JOHNSON & JOHNSON INC - US2012/252800, 2012, A1 Location in patent: Page/Page column 19

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