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Chemical Structure| 624741-83-9 Chemical Structure| 624741-83-9

Structure of 624741-83-9

Chemical Structure| 624741-83-9

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Product Details of [ 624741-83-9 ]

CAS No. :624741-83-9
Formula : C13H18BFO3
M.W : 252.09
SMILES Code : CC1(C)C(C)(C)OB(C2=CC=C(F)C=C2OC)O1
MDL No. :MFCD18732613
InChI Key :IYTUTWZXSBERDH-UHFFFAOYSA-N
Pubchem ID :22240091

Safety of [ 624741-83-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501

Application In Synthesis of [ 624741-83-9 ]

* 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 [ 624741-83-9 ]

[ 624741-83-9 ] Synthesis Path-Downstream   1~12

  • 2
  • [ 624741-83-9 ]
  • [ 1562338-65-1 ]
  • [ 1562342-42-0 ]
YieldReaction ConditionsOperation in experiment
620 mg With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; water; at 100℃; for 1h;Inert atmosphere; Microwave irradiation; To a microwave vial was added 2-(4-fluoro-2-methoxyphenyl)-4,4,5,5-tetramethyl-1 ,3,2-20 dioxaborolane (535 mg, 2.12 mmol), 6-chloro-N-methyi-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (Intermediate 1-1, 500 mg, 1.77 mmol), potassium phosphate (1.5 g, 7.07mmol), Pd2( dbah (162 mg, 0.18 mmol), and SPhos (72.6 mg, 0.18 mmol), followed by addition of1 ,4-dioxane (3.7 ml)/H20 (0.7 ml). The vial was purged with N2 for 5 minutes and the reactionmixture was heated at 1 oooe in the microwave for one hour. The reaction mixture was25 concentrated in vacuo. The crude material was adjusted to pH 3 using 1 M Hel aqueous solution,loaded on an sex column and washed with methanol, then eluted with 2 N ammonia in methanol.The product-containing fractions were concentrated to afford 6-(4-fluoro-2-methoxyphenyi)-Nmethyi-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (620 mg) MS [M+W] = 373.3.
  • 3
  • [ 450-88-4 ]
  • [ 73183-34-3 ]
  • [ 624741-83-9 ]
YieldReaction ConditionsOperation in experiment
63% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 80℃; for 16h;Inert atmosphere; 1-Bromo-4-fluoro-3-methoxybenzene (773 mg, 3.77 mmol) and bis(pinacolato)diboron (1.24 mg, 4.90 mmol) were dissolved in dioxane (10 mL), and anhydrous potassium acetate (1.11 mg, 11.31 mmol) and [1,1'-bis (diphenylphosphino)ferrocene]dichloropalladium.dichloromethane (276 mg, 0.377 mmol) were added. Under nitrogen gas atmosphere, the mixture was heated to 80 C. and stirred for 16 hours. After cooling to room temperature, the mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel TLC preparative plate (petroleum ether: ethyl acetate=1:1) to give compound 27-a (600 mg, yield 63%). 1H-NMR (400 MHz, CDCl3) δ: 7.65 (t, J=8.0 Hz, 1H), 6.55-6.66 (m, 2H), 3.82 (s, 3H), 1.34 (s, 12H) ppm
  • 4
  • [ 624741-83-9 ]
  • C17H21BrN6S [ No CAS ]
  • N-[7-(4-fluoro-2-methoxyphenyl)-6-methylthieno[3,2-d]pyrimidinyl-2-yl]-1-[3-(1-pyrrolidinyl)propyl]-1H-pyrazol-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
19.3% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 16h;Inert atmosphere; Compound 27-a (84 mg, 0.33 mmol), compound 26-a (70 mg, 0.16 mmol) and sodium carbonate (53 mg, 0.5 mmol) were suspended in dioxane (1.6 mL) and water (0.4 mL), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium.dichloromethane (12 mg, 0.016 mmol) was added. The reaction solution was purged with nitrogen gas for three times, heated to 80 C. and stirred for 16 hours. After cooling to the room temperature, the reaction was concentrated under reduced pressure, the residue was dissolved in dichloromethane (40 mL), then filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative HPLC (mobile phase: 0.05% aqueous ammonium bicarbonate solution: acetonitrile=40%-70%) to give 27 (15 mg, yield 19.3%). LC-MS (ESI): m/z=467[M+H]+. (0364) 1H-NMR (400 MHz, CDCl3) δ: 8.73(s, 1H), 7.79 (s, 1H), 7.42 (s, 1H), 7.34-7.40(m, 1H), 7.12 (s, 1H), 6.77-6.86 (m, 2H), 4.06(t, J=6.8 Hz, 2H), 3.76 (s, 3H), 2.43-2.51(m, 9H), 1.98-2.05 (m, 2H), 1.75-1.82 (m, 4H) ppm
  • 5
  • [ 624741-83-9 ]
  • C16H11FN2O [ No CAS ]
  • 6
  • [ 10495-73-5 ]
  • [ 624741-83-9 ]
  • C17H13FN2O [ No CAS ]
  • 7
  • [ 76-09-5 ]
  • [ 179899-07-1 ]
  • [ 624741-83-9 ]
  • 8
  • [ 456-49-5 ]
  • [ 25015-63-8 ]
  • [ 624741-83-9 ]
  • [ 628692-21-7 ]
  • C13H18BFO3 [ No CAS ]
  • 9
  • [ 624741-83-9 ]
  • [18F]1-fluoro-4-fluoro-5-methoxybenzene [ No CAS ]
  • 10
  • [ 624741-83-9 ]
  • tert-butyl 4-((4-(7-bromo-6-methylthieno[3,2-D]pyrimidin-2-yl)amino)-1-hydropyrazol-1-yl)piperidine-1-carboxylate [ No CAS ]
  • tert-butyl 4-(4-((7-(4-fluoro-2-methoxyphenyl)-6-methylthieno[3,2-D]pyrimidin-2-yl)amino)-1-hydropyrazol-1-yl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68.6% Add purified water (113Kg) and dioxane (390Kg) to the reaction kettle,4-(4-(7-Bromo-6-methylthieno[3,2-D]pyrimidin-2-yl)amino)-1hydro-pyrazol-1-yl)piperidine-1-tert-butyl carbonate Ester (37.26Kg, 93.65mol),2-Methoxy-4-fluorophenylboronic acid pinacol ester (23.05Kg, 120.22mol),Anhydrous potassium carbonate (20.95Kg, 151.8mol), palladium acetate (0.18Kg, 0.80mol)And 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (0.90Kg, 1.89mol). Under the protection of nitrogen, the temperature is controlled at 70±5 to react for 4 hours. Cool down to 40±5, add ammonia water (68Kg),Stir for 8 hours. Cool down to 20±5C and dilute with water (1110Kg).Dichloromethane extraction twice (244Kg, 170Kg). Combine the organic phases, wash sequentially with water and then with saturated brine. Add 3-mercaptopropyl ethyl sulfide-based silica (4.0Kg, used to remove heavy metal palladium) into the organic phase, and stir at 40±5C for 20 hours. After filtration, the filtrate was concentrated under reduced pressure. The remainder was slurried sequentially with methyl tert-butyl ether and ethanol. Filter, vacuum dry,Get tert-butyl 4-(4-((7-(4-fluoro-2-methoxyphenyl)-6-methylthieno[3,2-D]pyrimidin-2-yl)amino)-1-hydro-pyrazol-1-yl)piperidine-1-carboxylate 34.6Kg, yield: 68.6%.
  • 11
  • [ 624741-83-9 ]
  • 2-((6-chloropyrazin-2-yl)amino)-2-phenylethanol [ No CAS ]
  • 2-((6-(4-fluoro-2-methoxyphenyl)pyrazin-2-yl)amino)-2-phenylethanol [ No CAS ]
  • 12
  • [ 624741-83-9 ]
  • 4-chloro-2-(4-fluorophenyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one [ No CAS ]
  • 4-(4-fluoro-2-methoxyphenyl)-2-(4-fluorophenyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one [ No CAS ]
 

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