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[ CAS No. 1150114-75-2 ]

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Chemical Structure| 1150114-75-2
Chemical Structure| 1150114-75-2
Structure of 1150114-75-2 * Storage: {[proInfo.prStorage]}

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Product Details of [ 1150114-75-2 ]

CAS No. :1150114-75-2 MDL No. :MFCD06801704
Formula : C9H13BN2O2 Boiling Point : 421.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :192.02 g/mol Pubchem ID :46737701
Synonyms :

Safety of [ 1150114-75-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1150114-75-2 ]

  • Downstream synthetic route of [ 1150114-75-2 ]

[ 1150114-75-2 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 1150114-75-2 ]
  • [ 1222799-84-9 ]
  • [ 1222878-32-1 ]
  • 2
  • [ 1002127-25-4 ]
  • [ 1150114-75-2 ]
  • C23H23F3N2O2 [ No CAS ]
  • 3
  • [ 1268867-67-9 ]
  • [ 1150114-75-2 ]
  • [ 1268864-90-9 ]
  • 4
  • [ 1268867-67-9 ]
  • [ 1150114-75-2 ]
  • [ 1396750-22-3 ]
YieldReaction ConditionsOperation in experiment
55% With caesium carbonate; copper(l) chloride;1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; In N,N-dimethyl-formamide; at 100℃; for 0.5h;Inert atmosphere; Step 1. Methyl 3-(isopropyl(methyl)amino)-2-(6-(pyrrolidin- l-yl)pyridin-3-yl)quinoxaline-6- carboxylateTo a solution of 6-(pyrrolidin- l-yl)pyridin-3-ylboronic acid (244.9 mg, 1.28 mmol) in N,N- dimethylformamide (6 mL) was added 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6- carboxylate (170.0 mg, 0.58 mmol), Pd(OAc)2 (17.2 mg, 0.03 mmol), DPPF (28.3 mg, 0.05 mmol), CuCl (50.5 mg, 0.51 mmol) and Cs2CC>3 (332.4 mg, 1.02 mmol) with stirring for 0.5 h at 100C with an inert atmosphere of nitrogen. The reaction mixture was cooled and extracted with ethyl acetate (3 x 80 mL), dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was purified by a silica gel column with 2.5% ethyl acetate in petroleum ether to afford methyl 3-(isopropyl(methyl)amino)-2-(6-(pyrrolidin-l - yl)pyridin-3-yl)quinoxaline-6-carboxylate as a light yellow solid (130.0 mg, 55%).LC/MS (ES, m/z): [M+H]+ 406.0'H-NMR (300 MHz, DMSO) delta 8.69 (d, / = 2.1 Hz, 1H), 8.24 (d, / = 0.9 Hz, 1H), 8.08 (d, / = 2.4 Hz, 1H), 7.91 - 7.99 (m, 1H), 7.66 - 7.70 (m, 1H), 6.59 (d, / = 9.0 Hz, 1H), 4.22 - 4.31 (m, 1H), 3.92 (s, 3H), 3.40 - 3.49 (m, 4H), 2.71 (s, 3H), 1.93 - 1.99 (m, 4H), 1.18 (d, / = 6.6 Hz, 3H), 1.09 (d, / = 6.6 Hz, 3H)
YieldReaction ConditionsOperation in experiment
General procedure: A solution of 5-bromo-N,N-dimethylpyridin-2-amine (500 mg, 2.5 mmol) in THF (10 mL) was treated with n-BuLi (1.2 mL, 3 mmol) at -72 C. for 2 hours. Triisopropyl borate (705 mg, 3.75 mmol) was then added dropwise. After the completion of the addition, the mixture was stirred at -72 C. for an additional 1 hour and slowly warmed up and stirred at the ambient temperature overnight. MeOH was carefully added, and the volatiles were removed under reduced pressure to give the title compound. MS (m/z): 167 (M+H)+.
  • 6
  • [ 1192885-47-4 ]
  • [ 1150114-75-2 ]
  • 2-(3-(3-methoxy-5-methylphenyl)-4-(2-(6-(1-pyrrolidinyl)pyridin-3-yl)pyridin-4-yl)-1H-pyrazole-1-yl)acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; water; at 70℃; for 12.0h;Inert atmosphere; General procedure: A mixture of compound 4 (100 mg, 0.29 mmol), aryl boronic acid (0.35 mmol), bis(triphenylphosphine)palladium(II) dichloride (9 mg, 0.013 mmol) and K2CO3 (71 mg, 0.52 mmol) was placed in a mixed solvent of THF and water (4:1, v/v, 10 mL). N2 gas was bubbled into this mixture for 10 min, and then the mixture was heated at 70 C while stirring under N2 for 12 h. The reaction mixture was left to cool at room temperature, and extracted with ethyl acetate (100 mL × 3). The combined organic extracts were dried over anhydrous MgSO4 and evaporated under vacuum. The target compounds 5a-j were separated in pure form by column chromatography (silica gel) using the proper ratio of ethyl acetate and n-hexane.
  • 7
  • [ 1809-20-7 ]
  • [ 1150114-75-2 ]
  • diisopropyl (6-(pyrrolidin-1-yl)pyridin-3-yl)phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With triphenylphosphine; palladium dichloride; silver(l) oxide; at 100℃; for 2.0h;Inert atmosphere; General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with PdCl2 (15.9 mg,0.09 mmol, 15 mol %), PPh3 (314.7 mg, 1.2 mmol, 200mol %), Ag2O (278.1 mg, 1.2 mmol, 200 mol %), aryl (hetero)boronic acid (0.72 mmol, 1.2 equiv) and phosphite ester (0.6 mmol, 1.0 equiv), DMA(3.0 mL, without any purification) was added and the mixture was charged with N2 three times. The reaction mixture was then stirred at 100 C under N2 for 2h. The reaction progress was monitored by TLC. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, and washed with ethyl acetate. The yields of standard reaction were obtained by HPLC. The combined organic solvent was concentratedin vacuo. The residue was purified by silica gel flash chromatography to produce the desired product.
  • 8
  • [ 1150114-75-2 ]
  • [ 33443-53-7 ]
  • 4-phenyl-6-[6-(pyrrolidin-1-yl)pyridin-3-yl]quinazolin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; N,N-dimethyl-formamide; at 140℃;Microwave irradiation; General procedure: A mixture of 6-bromo-4-phenylquinazolin-2(1H)-one (200 mg, 0.66 mmol, 1 eq.), DMF (1.5 mL), H2O (0.6 mL), 4-pyridylboronic acid (106 mg, 0.864 mmol, 1.3 eq.), Pd(PPh3)4 (53 mg, 0.046 mmol, 0.07 eq.), and sodium carbonate (162 mg, 1.52 mmol, 2.3 eq.) in a microwave vessel (2 - 5 mL) was heated in the microwave at 140 C for 4 - 24 min. After completion of the reaction (monitored by LC/MS), the mixture was allowed to cool to room temperature, and H2O (8 mL) was added. The resulting precipitate was collected by vacuum filtration and washed with H2O and diethyl ether to afford the crude product as a solid. The crude product was dissolved in a minimal amount of 1,4-dioxane (1 - 10 mL) and any insoluble material was removed by vacuum filtration. A solution of HCl in dioxane (4.0 M) was then added dropwise until a precipitate was formed. The resulting precipitate was collected by vacuum filtration. All Suzuki reactions followed this general procedure, using the appropriate boronic acid, unless otherwise noted.
  • 9
  • 9-bromo-1-(3-(trifluoromethyl)phenyl)benzo[h][1,6]naphthyridin-2(1H)-one [ No CAS ]
  • [ 1150114-75-2 ]
  • 9-(6-(pyrrolidin-1-yl)pyridin-3-yl)-1-(3-(trifluoromethyl)phenyl)benzo[h][1,6]naphthyridin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.3% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 80℃; for 4.0h; General procedure: To a solution of compound 3(4.18 g, 10 mmol) in 1,4-dioxane at room temperature, we subsequentlyadded Pd(PPh3)4 (1.16 g, 1 mmol), K2CO3 (2.76 g, 20 mmol),and (2-oxoindolin-5 -yl)boronic acid (2.12 g, 12 mmol). Afterdegassing, the resulting mixture was heated to 80 C for 4 h beforecooling to room temperature. The solution was extracted withEtOAc. The organic layer was washed with water and brine, dried(MgSO4), filtered, and evaporated to dryness as a yellow solid. (3.89 g, 82.6% yield)
  • 10
  • [ 121-43-7 ]
  • [ 210963-93-2 ]
  • [ 1150114-75-2 ]
YieldReaction ConditionsOperation in experiment
53% Add SM17 (10.00g, 44.03mmol) to a 250ml three-necked flask containing THF (tetrahydrofuran) (50ml), add n-butyllithium (1.44g, 22.42mmol) dropwise at -78 C, and keep it for 1h after the addition Trimethyl borate (3.33g, 32.03mmol) was added dropwise, the temperature was continued for 1h, and the temperature was raised to room temperature and stirred overnight. Hydrochloric acid (2mol / L) was added to adjust the pH to neutral, and then filtered to obtain a crude white product, which was slurried with n-heptane to obtain a white solid intermediate I-P-1 (4.45g, yield 53%).
  • 11
  • [ 1150114-75-2 ]
  • C21H19BN2O3 [ No CAS ]
  • 12
  • [ 1150114-75-2 ]
  • C36H27N5O [ No CAS ]
  • 13
  • [ 86-76-0 ]
  • [ 1150114-75-2 ]
  • C21H18N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With tetrakis(triphenylphosphine) palladium(0); tetrabutyl-ammonium chloride; potassium carbonate; In ethanol; water; toluene; at 78℃; for 10.0h;Inert atmosphere; Intermediate IA (3.0g, 12.14mmol), intermediate IP-1 (3.11g, 16.18mmol), tetrakis (triphenylphosphine) palladium (0.70g, 0.61mmol), potassium carbonate (3.36g, 24.28mmol) , Tetrabutylammonium chloride (0.17g, 0.61mmol), toluene (30mL), ethanol (16mL) and deionized water (8mL) were added to the round bottom flask, heated to 78 C under nitrogen protection, and stirred for 10 hours; The reaction solution was cooled to room temperature, toluene (200 mL) was added for extraction, the organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure; the resulting crude product was purified by silica gel column chromatography using n-heptane as the mobile phase, and then used The dichloromethane / ethyl acetate system was purified by recrystallization to obtain the intermediate IP-2 (4.22 g, yield 83%
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