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Product Details of [ 1227911-51-4 ]

CAS No. :1227911-51-4
Formula : C14H19BN2O2
M.W : 258.12
SMILES Code : CC1(C)C(C)(C)OB(C2=CC3=C(C=C2)C(C)=NN3)O1
MDL No. :MFCD15071447
InChI Key :CHLPEMGHRXSNAA-UHFFFAOYSA-N
Pubchem ID :58504489

Safety of [ 1227911-51-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 1227911-51-4 ]

* 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 [ 1227911-51-4 ]

[ 1227911-51-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 7746-27-2 ]
  • [ 73183-34-3 ]
  • [ 1227911-51-4 ]
YieldReaction ConditionsOperation in experiment
91% With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; dichloromethane; at 80℃; for 12.5h;Inert atmosphere; Intermediate 97 3-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole To a solution of intermediate 95 (1.0 g, 4.73 mmoles) in Dioxan 16 ml), bis(pinacaloto)diboron (1.3 g, 5.21 mmoles) and potassium acetate (0.930 g, 9.47 mmoles) were added and the system is degassed for 30 min Bis(diphenylphosphinoferrocene)dichloro palladium.CH2Cl2 (0.387 g, 0.473 mmoles) was added under nitrogen atmosphere and heated to 80 C. After 12 h, the reaction mixture filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as off-white solid (1.1 g, 91% yield) which is used as such for the next step.
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere; Intermediate 126; 3-Methyl-6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-indazole; A mixture of <strong>[7746-27-2]6-bromo-3-methyl-1 H-indazole</strong> (8.32 g, 39.4 mmol), bis(pinacolato)diboron(11.01 g, 43.4 mmol, 1.1 equiv), potassium acetate (11.61 g, 118 mmol, 3 equiv) and PdCI2(dppf)«CH2CI2 adduct (1.61 g, 1.97 mmol, 0.05 equiv) in 1 ,4-dioxane (80 mL) was degassed and back flushed with argon. This action was repeated five times. The mixture was heated at 100 0C for 20 hours. After cooling to room temperature, the mixture was filtered through celite, and rinsed with EtOAc (200 mL). The filtrate was concentrated in vacuo, and the resulting residue was taken up in EtOAc (200 mL) and brine (50 mL), followed by filtration through celite. The filtrate was partitioned between phases, and the organic phase was treated with Darco and Na2SO4, filtered, and concentrated in vacuo. The residue was triturated in 30 mL of hexane, the resulting suspension was filtered, and the cake was washed with hexane (2 X 10 mL). Drying under vacuum at room temperature for 20 hours afforded the title compound (9.91 g) as a light pinkish solid. LC- MS (ES) m/z = 259 [M+H]+.
618 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 150℃; for 0.5h;Microwave irradiation; (1) Synthesis of 3-methyl-6-(4,4,5,5-tetramethyl[1,3,2]dloxaborolan-2-yl)-1H-indazole [5-1] (hereinafter referred to as a compound [5-1]) To a solution of <strong>[7746-27-2]6-bromo-3-methyl-1H-indazole</strong> (647 mg), which was obtained by the method described in the document (JP 2009-528363 W), in 1,4-dioxane (10 mL) were added bis(pinacolato)diboron (1.15 g), potassium acetate (899 mg) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (126 mg), and the mixture was subjected to microwave irradiation at 150C for 30min. The reaction mixture was quenched with water, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (618 mg) as a yellow solid. 1H-NMR (400 MHz, CDCl3) delta: 7.93 (1H, s), 7.67 (1H, dd, J = 8.1, 0.7 Hz), 7.55 (1H, d, J = 8.3 Hz), 2.60 (3H, s), 1.37 (12H, s).
 

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