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[ CAS No. 56311-13-8 ]

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Chemical Structure| 56311-13-8
Chemical Structure| 56311-13-8
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Product Details of [ 56311-13-8 ]

CAS No. :56311-13-8 MDL No. :MFCD08729295
Formula : C13H13BO2 Boiling Point : 384.898°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :212.05 g/mol Pubchem ID :-
Synonyms :

Safety of [ 56311-13-8 ]

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 [ 56311-13-8 ]

  • Downstream synthetic route of [ 56311-13-8 ]

[ 56311-13-8 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 2116-36-1 ]
  • [ 56311-13-8 ]
YieldReaction ConditionsOperation in experiment
(i) nBuLi, (ii) B(OiBu)3, (iii) aq. HCl; Multistep reaction;
  • 2
  • [ 90-90-4 ]
  • [ 56311-13-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N2H4*H2O, KOH / Heating 2: (i) nBuLi, (ii) B(OiBu)3, (iii) aq. HCl
  • 3
  • [ 870078-19-6 ]
  • [ 56311-13-8 ]
  • 1-[7-(4-benzyl-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-4-methyl-piperazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In 1,2-dimethoxyethane; ethanol; water at 90℃; for 19h; 4 General Procedure 2: Examples 4-13; Intermediate 8 (0.075 mmol) was dissolved in 0.5 mL of degassed EtOH and added to the corresponding boronic acid having the moieties-DR(at). Cesium carbonate (0.1875 mmol) was dissolved in degassed H20 and added to the reaction solution, followed by Pd(Ph3P)4 (0.00375 mmol) in 0.18 mL of degassed DME. The resultant mixture was then heated to 90 °C for 19 hours. The reaction was cooled and the crude material partitioned between 1.2 mL of 2 N NaOH and 2.3 mL of CH2CI2. The organics were extracted and then loaded onto an equilibrated 6-mL SCX-SPE cartridge (conditioned with one 5 mL wash with CH30H, and two rinses with 5 mL CH2CI2). The products were eluted with 7.5 mL of 1N triethylamine in CH30H collecting 1.25 mL fractions. The product containing fractions were dried under a N2 stream. Purifications were accomplished by HPLC separation on a Waters Symmetry C18 column (5mm, 30 x 150mm) with a 2.0 mL/min flow rate eluting with a gradient system of 100%, 80%, 0%, (0.1% TFA in H20/CH3CN) injecting each sample in 1.8 mL of DMSO (Table 2).
  • 4
  • [ 56311-13-8 ]
  • (S)-ethyl 2-(5-bromo-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate [ No CAS ]
  • ethyl (2S)-2-[5-(4-benzylphenyl)-4-(4,4-dimethylpiperidin-1-yl)-2,6-dimethylpyridin-3-yl]-2-(tert-butoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
54.8% With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In N,N-dimethyl-formamide at 110℃; for 2h; Inert atmosphere; (S)-Ethyl 2-(5-(4-benzylphenyl)-4-(4,4-dimethylpiperidin-l-yl)-2,6-dimethylpy 2-(tert-butoxy)acetate (S)-Ethyl 2-(5-(4-benzylphenyl)-4-(4,4-dimethylpiperidin-l-yl)-2,6-dimethylpy 2-(tert-butoxy)acetate: A mixture of (S)-ethyl 2-(5-bromo-4-(4,4-dimethylpiperidin-l-yl)- 2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate (0.0392 g, 0.086 mmol), (4- benzylphenyl)boronic acid (0.027 g, 0.129 mmol) and 2M Na2C03 (0.108 ml, 0.215 mmol) in DMF (2 mL) was degassed for 10 min. Then, Pd(Ph3P)4 (9.95 mg, 8.61 μιηο) added, degassed for 5 min and placed in a pre-heated oil bath at 110 °C. After 2 h, cooled and purified by prep-HPLC to afford (S)-ethyl 2-(5-(4-benzylphenyl)-4-(4,4- dimethylpiperidin-l-yl)-2,6-dimethylpyridin-3-yl)-2-(tert-butoxy)acetate (0.0256 g, 0.047 mmol, 54.8 % yield) as colorless paste. 1H NMR (500 MHz, CDC13) δ 7.24-7.33 (m, 4H), 7.19-7.24 (m, 4H), 7.09-7.12 (m, IH), 6.09 (s, IH), 4.13-4.30 (m, 2H), 4.08 (s, 2H), 3.17 (d, J=12.1 Hz, IH), 2.86 (t, J=l 1.7 Hz, IH), 2.61 (s, 3H), 2.26 (d, J=11.7 Hz, IH), 2.22 (s, 3H), 2.00 (t, J=11.4 Hz, IH), 1.54 (dt, J=4.2, 12.6 Hz, IH), 1.32-1.40 (m, IH), 1.26 (t, J=7.1 Hz, 3H), 1.21 (s, 9H), 1.17-1.20 (m, IH), 1.05 (d, J=11.4 Hz, IH), 0.90 (s, 3H), 0.61 (s, 3H). LCMS (M+H) = 543.5.
54.8% With tetrakis-(triphenylphosphine)-palladium; anhydrous sodium carbonate In N,N-dimethyl-formamide at 110℃; for 2h;
  • 5
  • [ 56311-13-8 ]
  • methyl 1-((2-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)methyl)cyclopropanecarboxylate [ No CAS ]
  • methyl 1-((2-(4-benzylphenyl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)methyl)cyclopropanecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 20 - 125℃; for 1h; Inert atmosphere; Methyl 1- ((2- (4-benzylphenyl’)- 7,8- dihydropyrido [4,3 - dl pyrimidin- 6 (5H)-yl’)methyl)cyclopropanecarboxylate This compound was prepared from compound XXc in a palladium mediated reaction as described in scheme 2, using (4-benzylphenyl)boronic acid instead of compound VI. Compound XXc (87 mg; 0.31 mmol; 1 eq) and (4- benzylphenyl)boronic acid (98 mg; 0.46 mmol; 1.5 eq) were dissolved in 4 mL DMF.Sodium carbonate (82 mg; 0.77 mmol; 2.5 eq) was added at RT and the mixture was degassed with argon (20 mi. Tetrakis(triphenylphosphine) -palladium(0) (17.8 mg; 0.015 mmol; 0.05 eq) was added and the mixture was stirred for lh at 125°C. The reaction mixture was evaporated, the residue was mixed with 40 mL ethyl acetate and 20 mL water. After phase separation, the ethy’ acetate phase was washed oncewith 10 mL water, dried with Mg504, filtered and evaporated. The residue was purified by flash chromatography (silica gel, DCM:MeOH) giving the product with a yield of 112 mg (0.295 mmol; 96%).
  • 6
  • [ 56311-13-8 ]
  • 5-chloro-3-iodofuro[3,2-b]pyridine [ No CAS ]
  • 3-(4-benzylphenyl)-5-chlorofuro[3,2-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 60℃; Inert atmosphere; General procedure A for Suzuki cross-coupling of 5-chloro-3-iodofuro[3,2-b]pyridine (9) atposition C-3. General procedure: A round-bottom flask with 5-chloro-3-iodofuro[3,2-b]pyridine (0.5 mmol), K3PO4 (1.75 mmol),Pd(dppf)Cl2 (0.025 mmol) and boronic acid/ester or potassium trifluoroborate salt (0.55 mmol)was three times evacuated and backfilled with argon. Degassed (by freeze-thaw-pump cycle)mixture of 1,4-dioxane/H2O (4 mL + 1 mL) was added and the reaction mixture was stirred at60 °C; the progress of the reaction was followed by TLC and/or by 1H NMR.
  • 7
  • 9-benzenesulfonyl-4-chloro-6-[4-(4-methylpiperazin-1-yl)phenyl]-9H-pyrido[2,3-b]indole [ No CAS ]
  • [ 56311-13-8 ]
  • 9-benzenesulfonyl-4-(4-benzylphenyl)-6-[4-(4-methylpiperazin-1-yl)phenyl]-9H-pyrido[2,3-b]indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane at 100℃; Inert atmosphere; 4.1. Chemistry All compounds are >95% pure by NMR and HR-MS analysis. Thesynthesis and chemical characterization of the compounds are detailedin the Supplementary Material. Typical experimental procedure: synthesisof compound 43 was obtained by sequential Suzuki-Miyauracoupling at positions 6 and 4 starting from the di-halogenated N-protectedprecursor 9-benzenesulfonyl-6-bromo-4-chloro-9H-pyrido [2,3-b]indole (Scheme 1). First, to a 0.03 M solution of precursor P1 in THF,under inert atmosphere and at room temperature, Pd(PPh3)4 (0.15equiv), K2CO3 (3 equiv) and the boronic pinacol ester (1.1 equiv) wereadded. The reaction mixture was stirred at 70 C for 4 h, then cooled toroom temperature. After purification by solvent extraction and precipitation,the 6-substituted product 9-benzenesulfonyl-6-(4’-(4′′ -methylpiperazinyl)phenyl)-4-chloro-9H-pyrido [2,3-b]indole, dissolved indioxane, was allowed to react with benzylphenyl boronic acid (2 equiv),Pd(PPh3)4 (0.15 equiv), and K2CO3 (3 equiv) overnight, at 100 C andunder inert atmosphere. Then the reaction mixture was cooled to roomtemperature and the 4,6-substituted product was purified by filtration,solvent extraction and precipitation. Finally, to afford the final compound43, sodium methoxide (15 equiv) was added to a solution of the4,6-substituted N-protected α-carboline in CH3OH/THF. The reactionmixture was allowed to stir at 65 C for 1.6 h, then cooled to roomtemperature and quenched with water. Compound 43 was obtainedafter solvent extraction (CH2Cl2/H2O) and precipitation in methanol.
With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In 1,4-dioxane at 100℃; Inert atmosphere; 4.1. Chemistry All compounds are >95% pure by NMR and HR-MS analysis. Thesynthesis and chemical characterization of the compounds are detailedin the Supplementary Material. Typical experimental procedure: synthesisof compound 43 was obtained by sequential Suzuki-Miyauracoupling at positions 6 and 4 starting from the di-halogenated N-protectedprecursor 9-benzenesulfonyl-6-bromo-4-chloro-9H-pyrido [2,3-b]indole (Scheme 1). First, to a 0.03 M solution of precursor P1 in THF,under inert atmosphere and at room temperature, Pd(PPh3)4 (0.15equiv), K2CO3 (3 equiv) and the boronic pinacol ester (1.1 equiv) wereadded. The reaction mixture was stirred at 70 C for 4 h, then cooled toroom temperature. After purification by solvent extraction and precipitation,the 6-substituted product 9-benzenesulfonyl-6-(4’-(4′′ -methylpiperazinyl)phenyl)-4-chloro-9H-pyrido [2,3-b]indole, dissolved indioxane, was allowed to react with benzylphenyl boronic acid (2 equiv),Pd(PPh3)4 (0.15 equiv), and K2CO3 (3 equiv) overnight, at 100 C andunder inert atmosphere. Then the reaction mixture was cooled to roomtemperature and the 4,6-substituted product was purified by filtration,solvent extraction and precipitation. Finally, to afford the final compound43, sodium methoxide (15 equiv) was added to a solution of the4,6-substituted N-protected α-carboline in CH3OH/THF. The reactionmixture was allowed to stir at 65 C for 1.6 h, then cooled to roomtemperature and quenched with water. Compound 43 was obtainedafter solvent extraction (CH2Cl2/H2O) and precipitation in methanol.
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