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Chemical Structure| 13061-96-6 Chemical Structure| 13061-96-6
Chemical Structure| 13061-96-6

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Product Details of Methylboronic acid

CAS No. :13061-96-6
Formula : CH5BO2
M.W : 59.86
SMILES Code : CB(O)O
MDL No. :MFCD00002105
InChI Key :KTMKRRPZPWUYKK-UHFFFAOYSA-N
Pubchem ID :139377

Safety of Methylboronic acid

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

Application In Synthesis of Methylboronic acid

* 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.

  • Upstream synthesis route of [ 13061-96-6 ]
  • Downstream synthetic route of [ 13061-96-6 ]

[ 13061-96-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 13061-96-6 ]
  • [ 885276-93-7 ]
  • [ 51135-70-7 ]
YieldReaction ConditionsOperation in experiment
77% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2 h; A solution of ethyl 5-bromopyrazolo[1,5-ajpyridine-3-carboxylate (1.0 g, 3.73 mmol),methylboronic acid (448 mg, 7.46 mmol), Pd(dppf)C12 (545 mg, 0.746 mmol) and C52CO3(2.42 g, 7.46 mmol) was dissolved in DMF (5.0 mL), then the mixture was stirred at 100 °Cfor two hours. It was concentrated, and purified by silica gel chromatography with PE:EA=5: 1to obtain the desired compound as an orange solid (589 mg, 77percent). ESI MS m/z = 204.5[M+Hj.
References: [1] Patent: WO2017/15449, 2017, A1, . Location in patent: Page/Page column 342.
  • 2
  • [ 13061-96-6 ]
  • [ 885523-35-3 ]
  • [ 180624-25-3 ]
References: [1] Patent: US2012/58986, 2012, A1, . Location in patent: Page/Page column 33.
[2] Patent: US2012/77797, 2012, A1, . Location in patent: Page/Page column 32; 33.
  • 3
  • [ 147497-32-3 ]
  • [ 13061-96-6 ]
  • [ 1082041-78-8 ]
YieldReaction ConditionsOperation in experiment
95.2% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 105℃; for 16 h; Inert atmosphere To a mixture of 6-bromo-3,4-dihydro-2H-isoquinolin-1-one (19.0 g, 82.4 mmol),CH3B(OH)2 (20.8 g, 329 mmol) and Na2CO3 (18.4 g, 165 mmol) in 1,4-dioxane (200 mL)and water (10.0 mL) is added [1,1’-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (2.46 g, 3.29 mmol) under a nitrogen atmosphere and the mixture is stirred at 105 °C for 16 hours under a nitrogen atmosphere. The suspension is filtered through a pad of diatomaceous earth and the filter cake is washed with DCM (3 x250 mL). The combined filtrates are washed with water (100 mL) and brine (80 mL), dried over Na2SO4, and the solvent isevaporated under reduced pressure. The crude product is purified by silica gel flash chromatography, eluting with a gradient of 0percent to 50percent EtOAc in PE to give the title compound (13.0 g, 95.2percent) as a yellow solid. ES/MS (m/z): 162.0 (M+H), ‘H NIVIR (400MHz, CDC13) 7.94 (d, J=8.0 Hz, 1H), 7.15 (d, J=7.8 Hz, 1H), 7.02 (s, 1H), 6.89 (br s, 1H),3.55 (dt, J=2.9, 6.6 Hz, 2H), 2.94 (t, J=6.5 Hz, 2H), 2.37 (s, 3H).
References: [1] Patent: WO2018/160406, 2018, A1, . Location in patent: Page/Page column 10; 11.
 

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