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[ CAS No. 1012785-44-2 ]

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Chemical Structure| 1012785-44-2
Chemical Structure| 1012785-44-2
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Product Details of [ 1012785-44-2 ]

CAS No. :1012785-44-2 MDL No. :MFCD09746204
Formula : C17H28BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :289.22 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1012785-44-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1012785-44-2 ]

  • Downstream synthetic route of [ 1012785-44-2 ]

[ 1012785-44-2 ] Synthesis Path-Downstream   1~13

YieldReaction ConditionsOperation in experiment
60%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; Inert atmosphere; Step 2: General procedure: To a solution of compound 1b-2 (1 g, 3.92 mmol) in DMF (20 mL) was added compound Pd(dppf)Cl2 (144 mg, 0.19 mmol), compound 1b.2 (1.2 g, 3.33 mmol) and potassium acetate (570 mg, 5.8 mmol), the mixture was stirred under argon atmosphere at 80° C. overnight. The reaction solution was concentrated and purified by combiflash to give compound 1b (400 mg, 31%). MS m/z (ESI): 304 [M+H]+.
  • 2
  • [ 1012785-44-2 ]
  • [ 1122-91-4 ]
  • [ 1260901-17-4 ]
YieldReaction ConditionsOperation in experiment
73% With tetrabutylammomium bromide; palladium diacetate; sodium carbonate In water at 150℃; for 0.166667h; Microwave irradiation; in air;
  • 3
  • [ 109-89-7 ]
  • [ 138500-85-3 ]
  • [ 1012785-44-2 ]
YieldReaction ConditionsOperation in experiment
100% With PS-NMM In tetrahydrofuran at 150℃; for 0.25h; Microwave irradiation; in air;
With potassium carbonate In acetonitrile at 20℃; for 4h; 5.1.5. General procedure D for synthesis of boric acid or borateester intermediates F and H General procedure: To a solution of 4-(bromomethyl) benzeneboronic acid pinacol ester (1.2 mmol, 1.0 equiv) and piperazine derivatives (1.56 mmol,1.3 equiv) in ACN (10 mL)was added K2CO3 (2.4 mmol, 2 equiv). Themixture was stirred at room temperature for 4 h, then the solvent was filtered. The filtrate was evaporated and then used in the next step without further purification.
  • 4
  • [ 589-15-1 ]
  • [ 1012785-44-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 2 h / 20 °C 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 2.5 h / 100 °C / Inert atmosphere
  • 5
  • [ 4885-19-2 ]
  • [ 73183-34-3 ]
  • [ 1012785-44-2 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; for 2.5h; Inert atmosphere; 4.2.2.1 N-(4-(6-bromoquinolin-4-yl)benzyl)-N-ethylethanamine (12a) To a stirred solution of 10 (1.00g, 4.00mmol) and K2CO3 (1.66g, 12.00mmol) in acetonitrile (20mL) was added dropwise diethylamine solution (1.20g, 16.00mmol) at room temperature for 2h. The solvent was evaporated in vacuo and the residue was then dissolved in EtOAc (50mL) and washed with water (20mL×3), the organic layers were washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to provide the 11a (0.83g, 84.7% yield) as an off-white liquid. (0041) Then, a mixture of 11a (0.83g, 3.43mmol), bis(pinacolato)diboron (0.96g, 3.77mmol), PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol) and potassium acetate (0.67g, 6.86mmol) in anhydrous 1,4-dioxane (15mL) was purged with argon and heated at 100°C for 2.5h. The reaction was then treated with 6 (1.20g, 3.60mmol), 2.0M aqueous Na2CO3 (5mL) and another portion of PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol), then heated at 110°C for 12h under argon. The reaction mixture was cooled to room temperature, filtered, and concentrated. The final compound was purified by MPLC (ISCO CombiFlash purification system) (MeOH/DCM, eluted from 0% to 10%), The fractions were collected, concentrated to afford 12a (0.72g, 57.2% yield).
  • 6
  • [ 1012785-44-2 ]
  • [ 927801-23-8 ]
  • N-(4-(6-bromoquinolin-4-yl)benzyl)-N-ethylethanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.72 g With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water;Inert atmosphere; Heating; To a stirred solution of 10 (1.00g, 4.00mmol) and K2CO3 (1.66g, 12.00mmol) in acetonitrile (20mL) was added dropwise diethylamine solution (1.20g, 16.00mmol) at room temperature for 2h. The solvent was evaporated in vacuo and the residue was then dissolved in EtOAc (50mL) and washed with water (20mL×3), the organic layers were washed with brine, and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to provide the 11a (0.83g, 84.7% yield) as an off-white liquid. (0041) Then, a mixture of 11a (0.83g, 3.43mmol), bis(pinacolato)diboron (0.96g, 3.77mmol), PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol) and potassium acetate (0.67g, 6.86mmol) in anhydrous 1,4-dioxane (15mL) was purged with argon and heated at 100C for 2.5h. The reaction was then treated with 6 (1.20g, 3.60mmol), 2.0M aqueous Na2CO3 (5mL) and another portion of PdCl2(dppf)-CH2Cl2 (0.084g, 0.103mmol), then heated at 110C for 12h under argon. The reaction mixture was cooled to room temperature, filtered, and concentrated. The final compound was purified by MPLC (ISCO CombiFlash purification system) (MeOH/DCM, eluted from 0% to 10%), The fractions were collected, concentrated to afford 12a (0.72g, 57.2% yield). 1H NMR (300MHz, CDCl3) delta 8.95 (d, J=4.4Hz, 1H), 8.09 (d, J=2.2Hz, 1H), 8.03 (d, J=9.0Hz, 1H), 7.79 (dd, J=9.0, 2.2Hz, 1H), 7.51 (d, J=8.3Hz, 2H), 7.45 (d, J=8.4Hz, 2H), 7.35 (d, J=4.4Hz, 1H), 3.81 (s, 2H), 2.69 (q, J=7.1Hz, 4H), 1.09 (t, J=7.1Hz, 6H). MS (ESI, positive ion) m/z: 369.71 (M+H+, 79Br), 371.71 (M+H+, 81Br).
  • 7
  • [ 106-38-7 ]
  • [ 1012785-44-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 3 h / Reflux; Inert atmosphere 2: potassium carbonate / acetonitrile / 2 h / 20 °C 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 2.5 h / 100 °C / Inert atmosphere
  • 8
  • [ 1012785-44-2 ]
  • N-(5-(4-(4-((diethylamino)methyl)phenyl)quinolin-6-yl)-2-methoxypyridine-3-yl)-2,4-difluorobenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water / Inert atmosphere; Heating 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 2.5 h / 100 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water / Inert atmosphere; Heating
  • 9
  • [ 1012785-44-2 ]
  • C26H33BN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water / Inert atmosphere; Heating 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / 1,4-dioxane / 2.5 h / 100 °C / Inert atmosphere
  • 10
  • [ 1012785-44-2 ]
  • (5-bromobenzofuran-3-yl)(3,4,5-tris(benzoxyl)phenyl)methanone [ No CAS ]
  • 5-[(5-{4-[(diethylamino)methyl]phenyl}-1-benzofuran-2-yl)carbonyl]benzene-1,2,3-triol hydrobromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: N-ethyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)ethanamine; (5-bromobenzofuran-3-yl)(3,4,5-tris(benzoxyl)phenyl)methanone With potassium carbonate In 1,4-dioxane; water for 0.333333h; Inert atmosphere; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 90℃; for 18h; General Procedure for the Removal of Benzyl Groups from 3.4.5- Tribenzyloxybenzenes (Procedure A) General procedure: A cooled (-70°C) stirred solution of tribenzyl oxybenzene (0.25mmol) in anhydrous DCM (5mL) under nitrogen was treated dropwise with 1N BBr3/DCM (0544) (l.5mL, l.5mmol), allowed to warm to room temperature and stirred at room temperature for 4 hours, then recooled (-60°C). The mixture was quenched dropwise with methanol (5mL), warmed to room temperature, stirred for 30 minutes, then concentrated in vacuo.
  • 11
  • [ 1012785-44-2 ]
  • (5-bromobenzofuran-3-yl)(3,4,5-tris(benzyloxy)phenyl)methanone [ No CAS ]
  • C47H43NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: N-ethyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)ethanamine; (5-bromobenzofuran-3-yl)(3,4,5-tris(benzyloxy)phenyl)methanone With potassium carbonate In 1,4-dioxane; water for 0.333333h; Inert atmosphere; Stage #2: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 90℃; for 18h; 5-r(5-(4-r(Diethylamino) l-benzofuran-2-yl )carbonyl1benzene- l 2.3-triol hydrobromide (APY-090) A stirred mixture of (5-bromobenzofuran-3-yl)(3,4,5- tris(benzyloxy)phenyl)methanone (l86mg, 0.30mmol), diethyl([4-(tetramethyl-l,3,2- dioxaborolan-2-yl)phenyl]methyl})amine (l22mg, 0.42mmol) and potassium carbonate (l66mg, l.2mmol) in 9: 1 dioxane/water (3mL) in a pressure tube was degassed over 20 minutes with argon, then treated with l,l-bis(diphenylphosphino)ferrocene dichloropalladium (11) (25mg, 0.034mmol), capped, and heated to 90°C for 18 hours and cooled to room temperature and diluted with DCM (l2mL) and filtered through Celite. The residual dark oil was dissolved in ethyl acetate and loaded onto a silica gel column (~50cc) and eluted with EtOAc, then 5% methanol/EtOAc to afford l87mg (89%) of the penultimate intermediate as an amber solid. A cooled (-70°C) stirred solution of this compound (l87mg, 0.266mmol) in anhydrous DCM (5mL) under nitrogen was subjected to Procedure A with 1N BBr3/DCM (l.6mL, l.6mmol), and the resultant solid triturated from DCM to afford lOOmg (73%) of 5-[(5-{4-[(diethylamino)methyl]phenyl}-l- benzofuran-2-yl)carbonyl]benzene-l,2,3-triol hydrobromide as a tan solid (Figure 7). NMR (d6-DMSO): d 9.20-9.50 (m, 3H), 7.80-8.20 (m, 4H), 7.62-7.70 (m, 2H), 7.38-7.55 (m, 2H), 7.09 (br s, 2H), 4.36 (d, J=6 Hz, 1H), 4.20-4.30 (m, 1H), 2.97-3.17 (m, 4H), 1.15-1.30 (m, 6H). 13C NMR (d6-DMSO): d 182.11, 155.20, 153.19, 146.18, 141.42, 139.88, 135.97, 132.33, 132.16, 129.60, 127.99, 127.83, 127.06, 121.93, 115.70, 113.11, 109.53, 54.95, 46.35, 8.84. LCMS m/z: [M-H] 429.7 (100%). LCMS m/z: [M+H]+ 431.7 (100%).
  • 12
  • [ 1012785-44-2 ]
  • 4-bromo-2,7-bis(3-morpholinopropyl)-9-((2-(pyrrolidin-1-yl)ethyl)amino)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone [ No CAS ]
  • 4-(4-((diethylamino)methyl)phenyl)-2,7-bis(3-morpholinopropyl)-9-((2-(pyrrolidin-1-yl)ethyl)amino)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)- tetraone [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; potassium carbonate In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere;
47% With (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; potassium carbonate In 1,4-dioxane; water at 80℃; for 16h; 5 Example 5: 4-(4-((diethylamino)methyl)phenyl)-2,7-bis(3-morpholinopropyl)-9- ((2-(pyrrolidin-1 -yl)ethyl)amino)benzo[imn]r3.8lphenanthroline-1.3.6.8(2H.7H)- tetraone A stirred mixture of 4-bromo-2,7-bis(3- morpholinopropyl)-9-((2-(pyrrolidin-1 - yl)ethyl)amino)benzo[lmn][3,8]phenanthroline- 1 ,3,6,8(2H,7H)-tetraone (155 mg, 0.218 mmol) and N-ethyl-N-(4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)benzyl)ethanamine (189 mg, 0.653 mmol) in dioxane (4 mL) was treated with potassium carbonate (436 mL of a 2 M aq solution, 0.871 mmol) and de-gassed. (0126) S-Phos Pd G3 (5.10 mg, 6.53 mmol) was charged, the mixture again de-gassed and the whole heated to 80 °C. After 16 hr, the mixture was allowed to cool then diluted with water (10 mL) and sat aq NaHCO3 (10 mL) and extracted with DCM (2 x 20 mL). The combined organics were dried over Na2SO4 and evaporated. Column chromatography (12 g BuchiFlashPure, 30-60% (9:1 DCM: 1.4 M NH3 in MeOH) in DCM, loading in DCM) gave product in moderate purity. The residue was purified by reverse phase column chromatography (12 g Reveleris C-18, 75- 100% (70 mM NH3 in MeOH) in water, loading in DMSO) to afford the product as a bright red glassy solid (81 mg, 47%). (0127) LCMS: Found m/z 794.2: (C45H60N7O6 (MH+) requires 794.5) 6.93 min. 1 H NMR (500 MHz, Methylene Chloride-d2) d 10.24 (t, J = 5.2 Hz, 1 H), 8.46 (s, 1 H), 8.32 (s, 1 H), 7.46 (d, J = 8.0 Hz, 2H), 7.33 (d, J = 8.0 Hz, 2H), 4.28 (t, J (0128) = 7.4 Hz, 2H), 4.13 (t, J = 7.4 Hz, 2H), 3.79 - 3.71 (m, 2H), 3.69 (s, 2H), 3.58 - 3.53 (m, 8H), 2.94 (t, J = 6.2 Hz, 2H), 2.69 - 2.66 (m, 4H), 2.61 (q, J = 7.1 Hz, 4H), 2.50 (t, J = 6.8 Hz, 2H), 2.47 - 2.30 (m, 10H), 1.93 (p, J = 6.9 Hz, 2H), 1.88 - 1.82 (m, 6H), 1.12 (t, J = 7.1 Hz, 6H).
  • 13
  • [ 1012785-44-2 ]
  • [ 283173-80-8 ]
  • 2-(4-((diethylamino)methyl)phenyl)-8-fluoro-4,5-dihydro-1H-azepino[5,4,3-cd]indol-6(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane at 90℃; for 2h; 5.1.2. General procedure A for synthesis of target compoundsY1-Y27, Y32-Y45 and Y50-Y53 General procedure: The boric acid or borate ester intermediates (B, D, F and H)(1.1 mmol, 1.1 eq), compound A (1 mmol, 1 eq), Na2CO3 (2 mmol, 2eq) and 10 mL dioxane were placed into a 50 mL three-neckedbottle, the reaction system was evacuated and backfilled withargon three times. Then Pd(dppf)Cl2 (0.05 mmol, 0.05 eq) wasadded to the reaction bottle under argon flow. The resulting solutionwasheated to 90 °C and stirred at this temperature for 2 h. The reactionwas monitored by TLC. The mixturewas diluted withwaterand extracted with ethyl acetate. The combined organic layers werewashed with brine, dried over anhydrous Na2SO4, and concentratedto give a crude product, which was purified by column chromatographyto give the target compounds.
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