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Chemical Structure| 1420998-43-1 Chemical Structure| 1420998-43-1

Structure of 1420998-43-1

Chemical Structure| 1420998-43-1

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Product Details of [ 1420998-43-1 ]

CAS No. :1420998-43-1
Formula : C13H20BNO3
M.W : 249.11
SMILES Code : CC1(C)C(C)(C)OB(C2=C(C)C=CN=C2OC)O1
MDL No. :MFCD16995670
InChI Key :GDEBIDFITKKLMA-UHFFFAOYSA-N
Pubchem ID :71241011

Safety of [ 1420998-43-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H320-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1420998-43-1 ]

* 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 [ 1420998-43-1 ]
  • Downstream synthetic route of [ 1420998-43-1 ]

[ 1420998-43-1 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 717843-51-1 ]
  • [ 73183-34-3 ]
  • [ 1420998-43-1 ]
YieldReaction ConditionsOperation in experiment
51% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 100℃; for 1.5 h; Inert atmosphere; Sealed tube Synthesis of intermediate V-d: 2-Methoxy-4-methyl-3-(4,4,5,5-tetramethyl-[l,3,2] dioxaborolan-2-yl)-pyridineA dry sealed tube under argon was charged with 3-bromo-2-methoxy-4-methylpyridine V-c (813 mg, 4.02 mmol), bis(pinacolato)diboron (1.12 g, 4.41 mmol), PdCl2(dppf :DCM (146 mg, 0.20 mmol), OAc (1.18 g, 12.0 mmol) and dry DMF (10 mL). After 1.5h at 100°C, the mixture was cooled to room temperature and a further portion of catalyst (75 mg, 0.092 mmol) was added. The tube was sealed and the mixture stirred at 100°C overnight. The mixture was cooled, the solvent evaporated and the mixture taken up in DCM before washing with water. The separated organics were dried (MgS0 ), filtered and evaporated before purification by column chromatography (Si02; 10percent to 20percent) EtOAc in cyclohexane) to afford the intermediate V-d as a mobile yellow oil (2.14g, 51percent). 1H NMR (300 MHz, CDC13) δ 8.00 (d, J = 5.3 Hz, 1H), 6.65 (d, J = 5.3 Hz, 1H), 3.89 (s, 3H), 2.33 (s, 3H), 1.40 (d, J = 11.1 Hz, 12H).
51% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 95℃; for 4 h; To a pressure tube was added 3-bromo-2-methoxy-4-methylpyridine (396 mg, 1.96 mmol), bis(pinacolato)diboron (597 mg, 2.35 mmol), Pd(dppf)2Cl2 (143 mg, 0.20 mmol), potassium acetate (384 mg, 3.92 mmol) and 1,4-dioxane (15 mL). The mixture was stirred at 95° C. for 4 hours. The residue was purified by silica gel flash chromatography (petroleum ether/ethyl acetate, 4:1) to give 2-methoxy-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (250 mg, 51percent yield) as a colourless oil. LCMS (ESI): [M+H]+=249.3.
References: [1] Patent: WO2013/14170, 2013, A1, . Location in patent: Page/Page column 78-80.
[2] Patent: US2018/282282, 2018, A1, . Location in patent: Paragraph 0843; 0844.
  • 2
  • [ 695-34-1 ]
  • [ 1420998-43-1 ]
References: [1] Patent: WO2013/14170, 2013, A1, .
  • 3
  • [ 13466-41-6 ]
  • [ 1420998-43-1 ]
References: [1] Patent: WO2013/14170, 2013, A1, .
  • 4
  • [ 18368-59-7 ]
  • [ 1420998-43-1 ]
References: [1] Patent: WO2013/14170, 2013, A1, .
 

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