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[ CAS No. 902148-83-8 ]

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Chemical Structure| 902148-83-8
Chemical Structure| 902148-83-8
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Product Details of [ 902148-83-8 ]

CAS No. :902148-83-8 MDL No. :MFCD11223187
Formula : C5H6BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :138.92 g/mol Pubchem ID :-
Synonyms :

Safety of [ 902148-83-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 902148-83-8 ]

  • Downstream synthetic route of [ 902148-83-8 ]

[ 902148-83-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 902148-83-8 ]
  • C29H20BrN3 [ No CAS ]
  • C34H24N4O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 120℃; for 6h; 17.A To a mixture of degassed 1 ,4-dioxane (13 mL) and water (3 mL) in a microwave vial was added [1 ,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(ll), complex with dichloromethane (0.026 g, 0.03 mmol), followed by the title compound from Preparative Example B (0.3 g, 0.612 mmol), (2-hydroxypyridin-4-yl)boronic acid (0.104 g, 0.75 mmol) and cesium carbonate (0.408 g, 1.15 mmol). The reaction mixture was then heated at ~120°C in a sand-bath for 6 hours. The reaction mixture was diluted with ethyl acetate (120 mL) and water (45 mL), the organic phase separated, dried over Na2S04, filtered and the solvents evaporated in vacuo. The dark residue was purified by chromatography on silica (25 g puriFlash, Interchim) using a Biotage Isolera system employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 100/0) to afford unreacted starting material B as off-white solid (0.1398 g, 47%). The gradient was then changed to dichloromethane/methanol (100/0 -> 95/5 -> 90/10 -> 80/20 -> 80/20) to afford the title compound as grey solid (0.0996 g, 32 %). 1H-NMR (400 MHz, DMSO-d6) δ = 11.52 (br-s, 1H), 9.43 (s, 1 H), 8.70 (d, 1 H), 8.23 (d, 1H), 7.97 (d, 1 H), 7.59-7.53 (m, 6H), 7.32-7.21 (m, 10H), 6.67 (d, 1H), 6.48 (d, 1 H), 6.19 (dd, 1 H) MS (ESI): m/z = 505.28 [M+Hf.
  • 2
  • [ 902148-83-8 ]
  • N-[(1R)-1-(3-bromophenyl)ethyl]-6,7-dimethoxy-2-methylquinazolin-4-amine [ No CAS ]
  • 4-(3-{(1R)-1-[(6,7-dimethoxy-2-methylquinazolin-4-yl)amino]ethyl}phenyl)pyridin-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With potassium phosphate; RuPhos precatalyst chloro(2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(ll) In water; N,N-dimethyl-formamide at 75℃; 388 Example 388 4-(3-{(1R)-1-[(6-dimethoxy-2-methylquinazolin-4-yl)amino]ethyl}phenyl)pyridin-2-ol General procedure: To a solution of 2-hydroxypyridine-4-boronic acid (46.8 mg, 0.32 mmol) and N-[(1 R)-1 -(3- bromophenyl)ethyl]-6,7-dimethoxy-2-methylquinazolin-4-amine (described in example 191, 100 mg, 0.25 mmol) in DMF (10 mL) were added potassium phosphate solution (0.5 M in water, 1.49 mL) and the second generation RuPhos precatalyst (chloro(2- dicyclohexylphosphino-2',6'-diisopropoxy-1,1 '-biphenyl)[2-(2'-amino-1,1 '- biphenyl)]palladium(ll), 38.6 mg, 0.05 mmol). The reaction mixture was stirred at 75°C for two hours. More 2-hydroxypyridine-4-boronic acid (46.8 mg, 0.32 mmol), chloro(2- dicyclohexylphosphino-2',6'-diisopropoxy-1,1 '-biphenyl)[2-(2'-amino-1,1 '- biphenyl)]palladium(ll) (38.6 mg, 0.05 mmol) and potassium phosphate solution (0.5 M in water, 1.49 mL) were added and the reaction was stirred at 75°C overnight. The reaction mixture was filtered and the filtrate was evaporated. The title compound was obtained in 12% yield (12.4 mg) after HPLC chromatography. 1H-NMR (400 MHz, DMSO-d6): δ [ppm] = 12.07- 1 1.09 (m, 1H), 8.02 (d, 1H), 7.78 (s, 1H), 7.70 (s, 1H), 7.58-7.49 (m, 2H), 7.48-7.38 (m, 2H), 7.02 (s, 1H), 6.56 (d, 1H), 6.47 (dd, 1H), 5.69 (t, 1H), 3.91 (s, 3H), 3.86 (s, 3H), 2.39-2.28 (m, 3H), 1.63 (d, 3H). LC-MS (Method 8): m/z: [M+H]+ = 417, Rt = 0.78 min.
  • 3
  • [ 902148-83-8 ]
  • (2-chloro-quinolin-4-yl)(5,6,7,8-tetrahydroquinolin-3-yl)methanone [ No CAS ]
  • (2-(2-hydroxypyridin-4-yl)quinolin-4-yl)(5,6,7,8-tetrahydroquinolin-3-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 120℃; for 2h; Microwave irradiation; 2 Example 2: Synthesis of (2-(2-hydroxypyridin-4-yl)quinolin-4-yl)(5,6,7,8-tetrahydroquinolin-3-yl)methanone 2-Hydroxypyridine-4-boronic acid (14.17 mmol), compound 4 (4.19 g, 12.98 mmol), Na2CO3 (4.51 g, 42.51 mmol), DME (22.95 mL) and H2O (5.67 mL) were added to a 50 mL microwave vial. The vial was degassed with N2 for 45 minutes. Then PdCl 2 (dppf) CH 2 Cl 2 (1.25 g, 1.70 mmol) adduct was added. The reaction mixture was heated at 120 ° C for 2 hours by microwave irradiation. The resulting mixture was diluted with ethyl acetate and filtered over EtOAc. It was then concentrated in vacuo. Purified by rapid chromatography, Using 0-100% ethyl acetate / heptane as eluent, Obtained as a white solid (2-(2-hydroxypyridin-4-yl)quinolin-4-yl)(5,6,7,8-tetrahydroquinolin-3-yl)methanone, 4.31 g, yield 87 %.
  • 4
  • [ 902148-83-8 ]
  • 3-chloro-6-({1-[4-(difluoromethyl)phenyl]-4-methyl-1H-1,2,3-triazol-5-yl}methoxy)pyridazine [ No CAS ]
  • 4-[6-({1-[4-(difluoromethyl)phenyl]-4-methyl-1H-1,2,3-triazol-5-yl}methoxy)pyridazin-3-yl]pyridin-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
4 mg With methanol; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3chloro-pyridyl)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 120℃; for 2h; Inert atmosphere; 2 4-[6-({1-[4-(difluoromethyl)phenyl]-4-methyl-1H-1,2,3-triazol-5-yl}methoxy)pyridazin-3-yl]pyridin-2-ol To (2-hydroxypyridin-4-yl)boronic acid (35 mg, 0.150 mmol) is added a solution of Example III.1 (37 mg, 0.100 mmol) in 0.5 mL methanol, 1 mL 1,4 dioxane, 2M aq sodium carbonate solution (0.10 ml, 0.200 mmol) and Pd-PEPPSI (1.68 mg 0.002 mmol) under argon and the reaction mixture is stirred for 2 h at 120° C. The mixture is purified by preparative HPLC to yield 4 mg of the product. ESI-MS: 411 [M+H]+
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