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[ CAS No. 591-50-4 ] {[proInfo.proName]}

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Chemical Structure| 591-50-4
Chemical Structure| 591-50-4
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Product Details of [ 591-50-4 ]

CAS No. :591-50-4 MDL No. :MFCD00001029
Formula : C6H5I Boiling Point : -
Linear Structure Formula :- InChI Key :SNHMUERNLJLMHN-UHFFFAOYSA-N
M.W :204.01 Pubchem ID :11575
Synonyms :

Calculated chemistry of [ 591-50-4 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.16
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.97
Log Po/w (XLOGP3) : 3.25
Log Po/w (WLOGP) : 2.29
Log Po/w (MLOGP) : 3.21
Log Po/w (SILICOS-IT) : 2.94
Consensus Log Po/w : 2.73

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.79
Solubility : 0.0333 mg/ml ; 0.000163 mol/l
Class : Soluble
Log S (Ali) : -2.92
Solubility : 0.243 mg/ml ; 0.00119 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.35
Solubility : 0.0907 mg/ml ; 0.000445 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.14

Safety of [ 591-50-4 ]

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

Application In Synthesis of [ 591-50-4 ]

* 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 [ 591-50-4 ]

[ 591-50-4 ] Synthesis Path-Downstream   1~80

  • 1
  • [ 591-50-4 ]
  • [ 7579-20-6 ]
  • [ 64021-70-1 ]
  • 2
  • [ 5093-70-9 ]
  • [ 591-50-4 ]
  • [ 3044-71-1 ]
  • 3
  • [ 591-50-4 ]
  • [ 1001-26-9 ]
  • [ 116519-41-6 ]
  • 4
  • [ 591-50-4 ]
  • [ 626-44-8 ]
  • [ 612-71-5 ]
  • 5
  • [ 591-50-4 ]
  • [ 201230-82-2 ]
  • [ 367-34-0 ]
  • N-(2,4,5-Trifluoro-phenyl)-benzamide [ No CAS ]
  • 6
  • [ 139-02-6 ]
  • [ 81447-67-8 ]
  • [ 101-84-8 ]
  • [ 591-50-4 ]
  • [ 625-95-6 ]
  • [ 3586-14-9 ]
  • 7
  • [ 58377-39-2 ]
  • [ 591-50-4 ]
  • [ 1625-91-8 ]
  • 9
  • [ 591-50-4 ]
  • [ 116632-40-7 ]
  • [ 19482-23-6 ]
  • 10
  • [ 1632-83-3 ]
  • [ 591-50-4 ]
  • [ 2622-63-1 ]
YieldReaction ConditionsOperation in experiment
97% With 10 molpercent nickel based 2,5-dihydroxyterephthalic acid metal organic framework-74; In diethylene glycol dimethyl ether; at 160℃; for 18h;Sealed tube; General procedure: In a typical experiment, a predetermined amount of Ni-MOF-74 was added to the 8 mL vial containing a mixture of iodobenzene (0.1030 g, 0.5 mmol), benzothiazole (0.1379 g, 1.0 mmol), Li2CO3 or KCl (1.0 mmol), and diphenyl ether (0.085 g, 0.5 mmol) as standard. 1-Methoxy-2-(2-methoxyethoxy)ethane (diglyme) (1 mL) was added and vial was tightly capped. Reaction mixture was heated at 160°C for 24 h. The catalyst loading was based on the molar ratio of nickel/iodobenzene. The reaction yield was monitored by withdrawing aliquots from the reaction mixture at different time intervals, diluting with ethylacetate (2 mL), quenching with an aqueous KOH solution (1percent, 1 mL), and then drying over anhydrous Na2SO4 before analyzing by GC with reference to diphenyl ether (internal equation with pure product), and further confirming product identity by GC?MS and NMR. To investigatethe recycle ability of Ni-MOF-74, the catalyst was filtered from the reaction mixture after the experiment, washed with ethylacetate, water, THF, and dried at 140°C under vacuum in 8 h. For the leaching test, a catalytic reaction was stopped after 12 h, analyzed by GC, and filtered to remove the solid catalyst. The reaction solution was then stirred for a further 12 h. Reaction progress, if any, was monitored by GC as previously described.
67% With (1-(2-(tert-butylamino)ethyl)-3-mesityl-2,3-dihydro-1H-imidazol-2-yl)copper(I) iodide; lithium tert-butoxide; In N,N-dimethyl-formamide; at 140℃; for 8h;Glovebox; General procedure: The product 12a is a representative reaction. To a vial (5 mL) containing caffeine (0.5 mmol), iodobenzene (1.0 mmol), catalyst 3e (0.05 mmol), and LiOtBu (1.0 mmol) was added DMF (1.0 mL) solvent under a glovebox atmosphere. After the substances were completely dissolved, the vial was screw-capped, taken outside the glovebox and heated at 140 °C for 8 h. The resulting mixture was filtered through Celite and washed with dichloromethane. The filtrate solution was concentrated in vacuo to afford the crude product, which was further purified by column chromatography using hexane/ethyl acetate as eluent to furnish 12a in 80percent yield.
46% With potassium phosphate; Cu2(4,4?-biphenyldicarboxylate)2(4,4?-bipyridine); In Hexadecane; N,N-dimethyl-formamide; at 120℃; for 3h;Green chemistry; General procedure: In a typical experiment, a pre-determined amount of Cu2(BPDC)2(BPY) was added to theflask containing a solution of iodobenzene (0.112 mL, 1 mmol),benzoxazole (0.238 g, 2 mmol), K3PO4(0.532 g, 2 mmol) and n-hexadecane (0.1 mL) as internal standard in DMF (4 mL). Thecatalyst concentration was calculated based on the molar ratio ofcopper/iodobenzene. The reaction mixture was stirred at 100Cunder an argon atmosphere for 180 min. The reaction conver-sion was monitored by withdrawing aliquots from the reactionmixture at different time intervals, quenching with an aqueousNaOH solution (5percent, 1 mL), drying over anhydrous Na2SO4, analyz-ing by GC with reference to n-hexadecane, and further confirmingproduct identity by GC?MS. To investigate the recyclability ofCu2(BPDC)2(BPY), the catalyst was filtered from the reaction mix-ture after the experiment, washed with copious amounts of DMF,dried under air at room temperature for 1 h, and reused if neces-sary. For the leaching test, a catalytic reaction was stopped after30 min, analyzed by GC, and filtered to remove the solid catalyst.The reaction solution was then stirred for a further 150 min. Reac-tion progress, if any, was monitored by GC as previously described.
  • 11
  • [ 591-50-4 ]
  • [ 188345-71-3 ]
  • N-(t-butyloxycarbonyl)-5-exo-phenyl-2-azabicyclo[2.2.1]heptane [ No CAS ]
  • N-(t-butyloxycarbonyl)-6-exo-phenyl-2-azabicyclo[2.2.1]heptane [ No CAS ]
  • 12
  • [ 591-50-4 ]
  • potassium <i>m</i>-cresolate [ No CAS ]
  • [ 3586-14-9 ]
  • 13
  • [ 591-50-4 ]
  • [ 108-39-4 ]
  • [ 3586-14-9 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 3h; General procedure: To prepare diaryl ethers using the Ullmann coupling reaction via O-arylation reactions, aryl halide (1 mmol), phenol derivative (1 mmol) and 0.2 g (1.5 mmol) of K2CO3 in DMF (5 mL) were placed into a round-bottom flask containing 0.05 g (0.02 mmol) of the catalyst. The above mixture was refluxed at 110 C for 3 h under vigorous stirring. When the reaction was complete, the reaction mixture was cooled and the solvent was removed under reduced pressure. Then, the mixture was diluted with CH2Cl2 and the catalyst was separated by an external magnet. The filtrate was evaporated on a rotary evaporator and the crude product was purified by column chromatography using ethyl acetate/n-hexane.
90% With caesium carbonate; In tetrahydrofuran; at 150℃; for 3h;Inert atmosphere;Catalytic behavior; General procedure: The catalytic O-arylation reactions were conducted in asealed stainless-steel reactor. A phenol (14 mmol), aryl halide(14 mmol), Cs2CO3 (14 mmol), tetrahydrofuran (THF, 10 mL),and the Cu2O/SiC catalyst (10 mg) were placed in the reactor.The reaction was performed under Ar at 150 C for 3 h. Afterthe reaction, the suspension was collected and centrifuged. Thesupernatant was analyzed using gas chromatography-massspectrometry (Bruker SCION SQ 456GC-MS, Germany). Theyields and TOFs were calculated based on the aryl halide usingthe following equations:Yield = Conversion (%) selectivity (%)= (1 - na/nb) x ntp/(ntp + nbp) x 100%TOF = Amount of aryl halides (mol) x conversion (%)x selectivity (%)/(mass of Cu2O/SiC (g) x Cu2O loading (%) xreaction time (h)/M[Cu2O] (g/mol))where na is the moles of aryl halide after reaction, nb is themoles of aryl halide before reaction, ntp is the moles of targetproduct after reaction, and nbp is the moles of byproduct afterreaction.
88% With copper(l) iodide; 1-(dimethylamino-1-yl-pyridin-2-yl-methyl)naphthalen-2-ol; potassium carbonate; In dimethyl sulfoxide; at 120℃; for 24h;Green chemistry;Catalytic behavior; General procedure: all reactions were carried out under air. Aryl halides (1.0 mmol) was treated with phenol (1.0 mmol) in the presence of 0.1 mmol CuI ,0.2 mmol 1-(alpha-aminobenzyl)-2-naphthols and 2.0 equiv K2CO3 in 3 mL DMSO at 120 for 24 h.The progress of the reaction was monitored by GC. After completion of the reaction, the catalyst was filtered easily and the product was extracted with EtOAc, The combined organic layers was dried over MgSO4 for 12 h. The solvent was evaporated under reduced pressure and the desired product purified by flash chromatography on a silica gel column using petroleum ether/ethyl acetate (10:1).
86% With copper(II) glycinate monohydrate; potassium hydroxide; In dimethyl sulfoxide; at 80℃; for 8h; General procedure: Experimental procedure for the synthesis of diaryl ether: To a stirred solution of iodo benzene (1.0 mmol) and phenol (1.0 mmol) in dry DMSO (2.0 ml) were added Cu catalyst 1 (0.02 mmol) and KOH (2.0 equiv) and the reaction mixture was heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After being cooled the reaction mixture at room temperature, the precipitated catalyst was separated by simple filtration and filtrate so obtained was diluted with ethyl acetate (10 ml). The organic layer was washed with water and dried over anhydrous Na2SO4. The solvent was evaporated under vacuum to give the crude product, which was purified by column chromatography with hexane as eluent to yield the expected product as yellowish oil. The products were analyzed by GC-MS, IR, 1H & 13C NMR analysis.
77% With copper(I) oxide; caesium carbonate; In N,N-dimethyl-formamide; at 140℃; for 24h;Inert atmosphere; Green chemistry; General procedure: In an oven-dried 50 mL round-bottomed flask with a condenser, phenol (1.0 mmol),bromobenzene (1.2 mmol), Cs2CO3 (1.0 mmol) and Cu2O/Cu-CNTs catalyst (0.06 g) were addedunder nitrogen atmosphere, followed by addition of DMSO (10 mL). The reaction mixture washeated in an oil bath at 140 and stirred at this temperature for 24 h. After the completion of thereaction (monitored by TLC), the reaction mixture was filtered. The filtrate was extracted withethyl acetate (3×10 mL) by adding a small amount of saturated aqueous NaCl solution. Theorganic layer was dried with anhydrous MgSO4 and concentrated to get the crude product. Theresulting residue was purified by column chromatography on silica gel to provide the desiredproduct.

  • 14
  • [ 591-50-4 ]
  • [ 869-19-2 ]
  • N-(N-phenyl-glycyl)-(L)-leucine [ No CAS ]
  • 15
  • [ 288-88-0 ]
  • [ 591-50-4 ]
  • [ 13423-60-4 ]
YieldReaction ConditionsOperation in experiment
96% With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In N,N-dimethyl-formamide; at 110℃; for 72h;Inert atmosphere; General procedure: A mixture of CuI (0.10 g, 0.50 mmol), the required azole(10 mmol), K3PO4 (4.4 g, 20 mmol), the required halide (12 mmol)and N,N0-dimethylethylenediamine (0.11 mL, 1.0 mmol) in DMF(5 mL) was degased and heated under argon at 110 C for 72 h.After filtration over celite (washing using AcOEt) and removal ofthe solvents, the crude product is purified by chromatography oversilica gel (the eluent is given in the product description). 4.3.1 1-Phenyl-1H-1,2,4-triazole (2a) Compound 2a was prepared from 1,2,4-triazole (0.69 g) and iodobenzene (1.4 mL) using the general procedure 1, and was isolated (eluent: heptane/AcOEt 7:3) in 96% yield as a yellow powder: mp 48 C (lit. 28 46 C); 1H NMR (CDCl3, 300 MHz) 7.42 (m, 1H), 7.53 (m, 2H), 7.71 (m, 2H), 8.15 (s, 1H), 8.74 (s, 1H); 13C NMR (CDCl3, 75 MHz) 120.1 (2CH), 128.3 (CH), 129.9 (2CH), 137.1 (C), 140.9 (CH), 152.7 (CH).
91% With caesium carbonate;copper(I) oxide; trans-N,N'-bis(pyridin-2-ylmethylene)cyclohexane-1,2-diamine; In DMF (N,N-dimethyl-formamide); at 50 - 82℃; for 24 - 72h;Conversion of starting material; Example 1.17 [0636] Preparation of 1-phenyl-1H-1,2,41 triazole [0637] Operating protocol A (82 C., 48 hours) was followed using 117 mg of Chxn-Py-Al (0.4 mmoles), 336 ?l of iodobenzene (3 mmoles), 138 mg of 1,2,4-triazole (2 mmoles), 1.042 g of caesium carbonate (3.2 mmoles) and 1.2 ml of DMF. [0638] The degree of transformation and selectivity were 100% and 98% respectively. [0639] The residue obtained following treatment was purified by silica gel chromatography (eluent: hexane/dichloromethane, 100/0 to 50/50). [0640] 264 mg of a dark yellow solid was obtained in a yield of 91%. [0641] Pale yellow needles were obtained after re-crystallisation from chloroform. [0642] The compound obtained had the following formula: [CHEMMOL-00056] [0643] The characteristics were as follows: [0644] MPt: 46 C. (CHCl3) (Lit: 46-47 C. given by Micetich, R G; Spevak, P; Hall, T W; Bains, B K; Heterocycles 1985, 23, 1645-1649); [0645] H NMR/CDCl3:? 8.52 (wide s, 1H, HI), 8.04 (wide s, 1H, H2), 7.53-7.65 (m, 2H, H4,8), 7.26-7.51 (m, 3H, H5,6,7); [0646] 13C NMR/CDCl3: ? 152.55 (C1), 140.88 (C2), 139.96 (C3), 129.73 (C5 and C7), 128.15 (C6), 119.99 (C4 and C8); [0647] GC/MS: Rt=14.02 min, M/Z=145, purity=100%; [0648] Rf=0.21 (eluent: dichloromethane/ethyl acetate, 90/10). Example 1.18 [0649] Preparation of 1-phenyl-1H-[1,2,4]triazole [0650] Operating protocol A (82 C., 24 hours) was followed using 117 mg of Chxn-Py-Al (0.4 mmoles), 336 ?l of iodobenzene (3 mmoles), 138 mg of 1,2,4-triazole (2 mmoles), 1.042 g of caesium carbonate (3.2 mmoles) and 1.2 ml of DMF. [0651] The degree of transformation and selectivity were 79% and 99% respectively. [CHEMMOL-00057] Example 1.19 [0652] Preparation of 1-phenyl-1H-[1,2,4]triazole Example 1.18 was repeated, operating at 50 C. (72 hours). The degree of transformation and selectivity for 1-phenyl-1H-[1,2,4-triazole] were 75% and 99% respectively. [0653] [CHEMMOL-00058]
91% Operating protocol A (82 C., 48 hours) was followed using 117 mg of Chxn-Py-Al (0.4 mmoles), 336 mul of iodobenzene (3 mmoles), 138 mg of 1,2,4-triazole (2 mmoles), 1.042 g of caesium carbonate (3.2 mmoles) and 1.2 ml of DMF. The degree of transformation and selectivity were 100% and 98% respectively. The residue obtained following treatment was purified by silica gel chromatography (eluent: hexane/dichloromethane, 100/0 to 50/50). 264 mg of a dark yellow solid was obtained in a yield of 91%. Pale yellow needles were obtained after re-crystallisation from chloroform. The compound obtained had the following formula: The characteristics were as follows: MPt: 46 C. (CHCl3) (Lit: 46-47 C. given by Micetich, R G; Spevak, P; Hall, T W; Bains, B K; Heterocycles 1985, 23, 1645-1649); 1H NMR/CDCl3: delta8.52 (wide s, 1H, H1), 8.04 (wide s, 1H, H2), 7.53-7.65 (m, 2H, H4,8), 7.26-7.51 (m, 3H, H5,6,7); 13C NMR/CDCl3: delta 152.55 (C1), 140.88 (C2), 139.96 (C3), 129.73 (C5 and C7), 128.15 (C6), 119.99 (C4 and C8); GC/MS: Rt=14.02 min, M/Z=145, purity=100%; Rf=0.21 (eluent: dichloromethane/ethyl acetate, 90/10). Example 1.18; Preparation of 1-phenyl-1H-[1,2,4]triazole; Operating protocol A (82 C., 24 hours) was followed using 117 mg of Chxn-Py-Al (0.4 mmoles), 336 mul of iodobenzene (3 mmoles), 138 mg of 1,2,4-triazole (2 mmoles), 1.042 g of caesium carbonate (3.2 mmoles) and 1.2 ml of DMF. The degree of transformation and selectivity were 79% and 99% respectively. ; Example 1.19; Preparation of 1-phenyl-1H-[1,2,4]triazole; Example 1.18 was repeated, operating at 50 C. (72 hours). The degree of transformation and selectivity for 1-phenyl-1H-[1,2,4-triazole] were 75% and 99% respectively.
87% With potassium phosphate; In N,N-dimethyl-formamide; at 110℃; General procedure: 1 mmol of the compound of the formula II-1 and 2 mmol of the compound of the formula III are sequentially added to the reaction.0.5mmol% catalyst CS Cu2O,3mmol potassium phosphate and 0.5ml N,N-dimethylformamide solution, heated to 110 C to stir the reaction,After the TLC reaction was completed, the reaction was quenched with water and filtered for ethyl acetate.Washed with saturated brine, dried and concentrated.The product was obtained by silica gel column chromatography.
83% With caesium carbonate;iron(III) acetylacetonate; copper(II) oxide; In N,N-dimethyl-formamide; at 90℃; for 30h;sealed tube;Conversion of starting material; Preparation of 1-phenyl-1H-[1,2,4]triazole [0220] Following General Procedure A (90 0C, 30 hours), 1/-/-[1 ,2,4]triazole (104 mg, 1.5 mmol) is coupled with iodo-benzene (112 muL, 1.0 mmol). The crude brown oil is purified by flash chromatography on silica gel (eluent: dichloromethane/hexanes = 50/50) to provide 120 mg (83 % isolated yield) of the desired product as a light yellow solid. <n="50"/>007/001836_ 49 -IdentificationMp: 460C.1H NMR (400 MHz, CDCI3): delta 8.49 (s, 1 H1 H8), 8.03 (s, 1H, H7), 7.58-7.61 (m, 2H, H2i6), 7.40-7.44 (t, 2H1 H3,5), 7.31-7.33 (t, 1 H, H4).13C NMR (100 MHz, CDCI3): delta 152.62 (C7), 140.91 (C8), 136.99 (C1), 129.77 (C3,5), 128.21 (C4), 120.04 (C2i6).IR (KBr) : v (cm'1) = 3105, 2924, 2852, 1600, 1514, 1416, 1359, 1278, 1223,1152, 1055, 981 , 876, 754, 681 , 671 , 503.GC/MS: rt = 15.28 min, M/Z = 145.HRMS: 146.0721 (M+H). Theoretical: 146.0718
71% A flask was charged with K2CO3 (12.1689 g, 88 mmol), 1H-1,2,4-triazole (2.0042 g, 29 mmol), Cu2O(430 mg, 3 mmol) and 1,10-phenanthroline (1.0452 g, 5.8 mmol) and then evacuated and back-filled with N2. Then, anhydrous DMF (20 ml) and iodobenzene (8.9764 g, 4.92 ml, 44 mmol) were added and the resulting mixture was heated to 120 C for 64 h and then diluted with CH2Cl2 (40 ml). The mixture was filtered through a pad of Celite and the residue washed with CH2Cl2 (20 ml). The resulting organic layer was washed with water (20 ml) and brine (20 ml), dried over MgSO4 and concentrated under reduced pressure. The crude mixture was purified by column chromatography (cyclohexane/ethyl acetate 8/0?2/0) to yield the product as a pale yellow solid (2.986 g, 71%).
65% EXAMPLE 108 1-phenyltriazole 1 g (0.0145 mol) triazole 2, 0.21 g (0.00145 mol) copper(I)oxide, 0.29 g (0.00145 mol) phenantroline monohydrate and 6.01 g (0.044 mol) potassium carbonate are weighed into a Schlenk flask. After repeated evacuating and flushing with argon, 10 ml dry DMF is added. Evacuating and flushing with argon are repeated several times. Subsequently, 2.42 ml (4.43 g, 0.022 mol) of iodobenzene is added. The reaction mixture is stirred for 48 h at 100 C. under argon. After cooling 20 ml DCM is added and filtered. The solvent is removed in vacuum and the product is obtained after purification by column chromatography (KG 60, gradient petroleum ether/EtOAc 8:2 to EtOAc) as a yellowish-white solid.M 145.17 C8H7N3 Yield: 1.362 g (65%)1H-NMR DM-94 (300 MHz/DMSO): (ppm)=7.41 (t, 1H, 6-H); 7.58 (t, 2H, 5/5'-H); 7.87 (d, 2H, 4-H); 8.25 (s, 1H, 1-H); 9.31 (s, 1H, 2-H)13C-NMR DM-94 (75.475 MHz/DMSO): (ppm)=119.37 (5/5'-C); 127.78 (6-C); 129.77 (4/4'-C); 136.74 (3-C); 142.27 (2-C); 152.39 (1-C)

Reference: [1]Journal of the American Chemical Society,2007,vol. 129,p. 13879 - 13886
[2]Journal of Organic Chemistry,2007,vol. 72,p. 2737 - 2743
[3]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6355 - 6363
[4]RSC Advances,2014,vol. 4,p. 44105 - 44116
[5]Journal of Organic Chemistry,2004,vol. 69,p. 5578 - 5587
[6]Synlett,2008,p. 614 - 620
[7]Organic and Biomolecular Chemistry,2016,vol. 14,p. 10861 - 10865
[8]Chemistry - A European Journal,2004,vol. 10,p. 5607 - 5622
[9]Patent: US2003/236413,2003,A1 .Location in patent: Page 24-25
[10]Patent: US2005/234239,2005,A1 .Location in patent: Page/Page column 23; 28-29
[11]Synthesis,2008,p. 1707 - 1716
[12]ChemPlusChem,2013,vol. 78,p. 1491 - 1502
[13]Patent: CN109608401,2019,A .Location in patent: Paragraph 0070; 0071; 0072
[14]RSC Advances,2014,vol. 4,p. 7321 - 7329
[15]Angewandte Chemie - International Edition,2007,vol. 46,p. 934 - 936
[16]Patent: WO2008/4088,2008,A2 .Location in patent: Page/Page column 48-49
[17]Synthesis,2010,p. 1505 - 1511
[18]Chemistry - An Asian Journal,2014,vol. 9,p. 166 - 178
[19]Advanced Synthesis and Catalysis,2007,vol. 349,p. 2673 - 2676
[20]Tetrahedron,2013,vol. 69,p. 5647 - 5659
[21]Journal of Organic Chemistry,2011,vol. 76,p. 305 - 308
[22]Patent: US2011/105761,2011,A1 .Location in patent: Page/Page column 38-39
[23]Chemical Communications,2019,vol. 55,p. 3805 - 3808
[24]Asian Journal of Chemistry,2013,vol. 25,p. 5647 - 5648
[25]Advanced Synthesis and Catalysis,2008,vol. 350,p. 1253 - 1257
[26]Tetrahedron Letters,2007,vol. 48,p. 6573 - 6576
[27]Advanced Synthesis and Catalysis,2019,vol. 361,p. 4342 - 4353
[28]Inorganic Chemistry,2019,vol. 58,p. 1935 - 1948
  • 16
  • [ 591-50-4 ]
  • [ 171596-36-4 ]
  • (6R,12AR)-6-benzo[1,3]dioxol-5-yl-2-phenyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]-pyrido[3,4-b]indole-1,4-dione [ No CAS ]
  • 17
  • [ 591-50-4 ]
  • potassium hexacyanoferrate (II) [ No CAS ]
  • [ 57103-20-5 ]
  • 18
  • [ 1126-09-6 ]
  • [ 591-50-4 ]
  • [ 94201-40-8 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;bis(tri-t-butylphosphine)palladium(0); In 1,2-dimethoxyethane; at 100℃; for 14.0h; A. To a solution of ethyl isonipecotate (1.00 g, 6.36 mmol) in 10 mL of anhydrous DME was added iodobenzene (1.95 g, 9.54 mmol), bis(tri-t-butylphosphine)palladium(0) (0.33 g, 0.636 mmol), and potassium phosphate (2.70 g, 12.7 mmol). The reaction mixture was heated to 100° C. and stirred for 14 hours. Solids were filtered off from the resulting mixture and the collected filtrate was concentrated under reduced pressure to provide the crude product, which was then redissolved into 10 mL of methanol. 2 mL of 1N lithium hydroxide was added to hydrolyze the ester at 80° C. for 3 hours. Solvent was evaporated off and the basic residue was acidified by 2N HCl. The aqueous mixture was extracted with EtOAc. The combined organic layers was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to afford the crude product which was then purified by flash column chromatography with CH2Cl2 and MeOH to yield 1-phenyl-piperidine-4-carboxylic acid as yellow solid.
  • 19
  • [ 591-50-4 ]
  • [ 2401-21-0 ]
YieldReaction ConditionsOperation in experiment
25.9 g (94.2%) With chlorine; In chloroform; EXAMPLE 6 Preparation of iodobenzene dichloride. Chlorine gas is bubbled through a solution of iodobenzene (20.4 g; 0.1 mole) in chloroform (100 ml) while the temperature of the reaction mixture is maintained at -5° C. In about 10 minutes a yellow solid precipitates and is removed by filtration. The filtrate is then further treated with chlorine gas until the formation of yellow solid ceases. The solid fractions are combined and air dried to afford 25.9 g (94.2percent) of title product.
  • 21
  • [ 591-50-4 ]
  • [ 4347-31-3 ]
  • [ 26170-85-4 ]
  • 22
  • [ 591-50-4 ]
  • [ 52522-41-5 ]
  • [ 13406-29-6 ]
  • [ 180891-57-0 ]
  • 23
  • [ 591-50-4 ]
  • [ 63902-12-5 ]
  • cesium pivalate [ No CAS ]
  • [ 13406-29-6 ]
  • [ 851530-55-7 ]
  • 24
  • [ 52522-40-4 ]
  • [ 591-50-4 ]
  • [ 119072-54-7 ]
  • [ 926042-20-8 ]
  • 25
  • [ 52522-40-4 ]
  • [ 591-50-4 ]
  • [ 198766-52-8 ]
  • [ 603-32-7 ]
  • [ 352670-77-0 ]
  • [ 942472-59-5 ]
  • [ 36234-31-8 ]
  • rac-2,2'-bis[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]-1,1'-biferrocene [ No CAS ]
  • 26
  • [ 52522-40-4 ]
  • [ 591-50-4 ]
  • [ 2359-97-9 ]
  • [ 956274-07-0 ]
  • 27
  • [ 591-50-4 ]
  • [ 6825-20-3 ]
  • [ 57103-20-5 ]
YieldReaction ConditionsOperation in experiment
85% With copper(l) iodide; 18-crown-6 ether; potassium carbonate; In DMPU (1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone); at 170℃; for 20h; Synthesis of Intermediate E; 3.25 g (10.0 mmol) of 3, 6-dibromocarbazole, 10.2 g (50.0 mmole) iodobenzene, 190 mg (1.0 mmole) of Cul, 132 mg (0.5 mmole) of 18-C-6, 2.76 g (20.0mmole) of K2CO3 were dissolved in 50 mL of DMPU, and stirred at 170°C for 20 hours. The mixture was cooled to room temperature and 50 mL of diethylether was added thereto. Then the mixture was washed with plenty of water and ammonium hydroxide solution. A collected organic layer was dried over MgSO4 to evaporate the solvent. The residue was purified using silica gel column chromatography to obtain 3.40 g of white solid Intermediate E (Yield: 85 percent). (NMR (CDCl3, 400MHz) delta (ppm) 7.92 (m, 2H), 7.55-7.47 (m, 6H), 7.36-7.16 (m, 3H); 13C NMR (CDCl3, 100MHz) delta (ppm) 142.6, 137.6, 130.2, 129.8, 127.4, 127.0, 122.8, 122.5, 115.3, 111.3).
75% With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate; In toluene; at 100℃; for 24h; To a round bottom flask Sub 2-1-6 (6.5g, 20mmol), Sub 2-1-2-1 (4.1g, 20mmol),Pd2 (dba) 3 (0.9g, 1mmol), PPh3 (0.5g, 2mmol ), NaOt-Bu (5.8g, 60mmol), were addedto toluene (210mL), respectively, and refluxed under stirring for 24 hours at 100 ° C.The organic layer was dried and the ether was extracted with water over MgSO4 andconcentrated and to the resulting organic silicagel column and recrystallized from a Sub2-1-7-1 6.0g (yield: 75percent) was obtained.
3.27 g With palladium diacetate; tris-(o-tolyl)phosphine; sodium t-butanolate; In toluene; 2.5 g (14.9 mmol) ofcarbazole was used (utilized) to perform an NI3S bromination to synthesize 2,5-dibromocar- bazole. Then, the 2,5-dibromocarbazole and iodinated phenyl were used (utilized) to synthesize 3.72 g (9.28 mmol) of Intermediate E through a buchwald reaction.
  • 28
  • [ 591-50-4 ]
  • [ 69655-76-1 ]
  • POSS-F [ No CAS ]
  • 29
  • [ 90560-10-4 ]
  • [ 591-50-4 ]
  • [ 92014-01-2 ]
YieldReaction ConditionsOperation in experiment
Example 16 [00381] Step 1 [00382] 1-(2,2-Diethoxy-ethylsulfanyl)-3-methoxy-benzene. To a solution of 3-methoxybenzenethiol (15.0 mL, 120 mmol) and potassium carbonate (16.6 gm, 120 mmol) in 150 mL of acetone at room temperature was added dropwise 2-bromo-1,1-diethoxy-ethane (16.5 mL, 110 mmol). The reaction mixture was stirred at room temperature for 16 hours. The solids in the reaction mixture were removed by filtration and were washed well with acetone. The filtrate was concentrated. The residue was diluted with water and extracted several times with ether. The ether layers were combined and washed with 0.5 M KOH, water, brine, and were then dried over anhydrous sodium sulfate, filtered, and concentrated to yield 28.2 gm of the title compound. [00383] Step 2 [00384] 6-Methoxy-benzo[b]thiophene. To a solution of boron trifluoride etherate (14.45 mL, 115 mmol) in 2000 mL of methylene chloride stirring in a cold water bath 20° C. was added dropwise 1-(2,2-Diethoxy-ethylsulfanyl)-3-methoxy-benzene (28.2 gm, 110 mmol) dissolved in 500 mL of methylene chloride. The addition was complete in 3 hrs. and then the reaction was warmed to room temperature for a further 1.5 hrs. The reaction mixture was then quenched with saturated sodium bicarbonate solution. The organic layer was separated and the aqueous layer was back extracted several times with methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was chromatographed on silica gel (using a gravity column) using hexanes as the eluant to yield 10.9 gm of the title compound. [00385] General Procedure for the Synthesis of Compunds of Formula IV [00386] The general scheme is outlined in Scheme 8b. Three sets of conditions are used for the acylation step and they are described below. Table 2 lists the compounds with relevant data and which procedure was used in each case. [00387] Step 3 [00388] 6-Methoxy-2-phenyl-benzo[b]thiophene. To a solution of 6-Methoxy -benzo[b]thiophene (250 mg, 1.52 mmol) in 3.7 mL THF at -20° C. was added dropwise n-butyllithium (0.67 mL, 1.67 mmol). The mixture was stirred at 0° C. for 1.5 hrs. and at room temperature for 0.5 hrs. Anhydrous zinc chloride (269 mg, 1.97 mmol) in 1.9 mL of THF was added by cannula to the reaction. The reaction was then stirred at room temperature for 15 minutes and then Pd(Ph3P)4 (70 mg, 0.06 mmol) and iodobenzene (0.22 mL, 1.97 mmol) were added and the reaction stirred at room temperature for 3 hrs. Other aromatic or heteroaromatic bromides, iodides or triflates can replace iodobenzene in this procedure. If a triflate is used 3 equivalents of anhydrous lithium chloride must be added. The reaction can be refluxed overnight to push it towards completion. The solvent was evaporated and the residue was diluted water and extracted into ethyl acetate. The combined organic layers was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was chromatographed on silica gel using 100percent Hexanes to 1percent ethyl acetate/hexanes as the gradient eluant to yield 250 mg of the title compound. [00389] Acylation Procedure A [00390] Step 4 [00391] (6-Hydroxy-2-phenyl-benzo[b]thiophen-3-yl)-[4-(2-piperidin-1-yl-ethoxy) -phenyl]-methanone. A solution of the product from Step 3, Example 16 (272 mg, 1.13 mmol), 4-(2-Piperidin-1-yl-ethoxy)-benzoyl chloride (7.9 mL, 1.53 mmol), and titanium tetrachloride (6.62 mL, 5.66 mmol) in 16.5 mL of methylene chloride was stirred at room temperature for 6 hrs. To demethylate, ethanethiol (0.335 mL, 4.53 mmol) and AlCl3 (600 mg, 4.53 mmol) in two portions were added to the reaction and it was stirred for an additional 2.5 hrs. The reaction was quenched with saturated sodium bicarbonate solution and the solution was extracted twice with methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was chromatographed on silica gel using 1percent MeOH: CH2Cl2 to 5percent MeOH CH2Cl2 as the gradient eluant to obtain 231 mg of the title compound. [00392] 1H NMR (MeOH-d4) delta7.70(d, 2H), 7.40(m, 3H), 7.30(d, 1H), 7.25(m, 3H), 6.90(d, 1H), 6.85(d, 2H), 4.15(t, 2H), 2.75(t, 2H), 2.55(m, 4H), 1.60(m, 4H), 1.50(m, 2H)
  • 30
  • [ 591-50-4 ]
  • [ 143360-89-8 ]
  • [ 3469-20-3 ]
  • 31
  • [ 591-50-4 ]
  • [ 886766-28-5 ]
  • [ 1254981-66-2 ]
YieldReaction ConditionsOperation in experiment
31% With cesium hydroxide; In dimethyl sulfoxide; at 120℃; for 0.666667h;Sealed tube; A stirred solution of <strong>[886766-28-5]4,7-diaza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester</strong> (0.1 g, 0.471 mmol) [C.A.S. 886766-28-5] , iodobenzene (0.026 ml, 0.236) and CsOH (0.079 g, 0.471 mmol) in DMSO (1 ml) was heated in a sealed tube at 1200C for 20 min. After cooling, additional <strong>[886766-28-5]4,7-diaza-spiro[2.5]octane-7-carboxylic acid tert-butyl ester</strong> (2 eq.) was added, and the mixture was then heated at 1200C for 20 min. The mixture was cooled.The mixture was washed with NH4Cl (aqueous sat. solution) was added and extracted with Et2O. The organic phase was separated, washed with water, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by manifold (Sep-Pak.(R). silica cartridge; DCM as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate D61 (0.021 g, 31percent) as a white solid.
  • 32
  • [ 591-50-4 ]
  • [ 1569-16-0 ]
  • [ 1256347-50-8 ]
  • 34
  • [ 591-50-4 ]
  • [ 70357-66-3 ]
  • [ 70357-61-8 ]
  • 35
  • [ 591-50-4 ]
  • [ 6358-06-1 ]
  • 4-chloro-3-phenoxybenzenamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With 2-Picolinic acid; potassium phosphate; copper(l) iodide; In dimethyl sulfoxide; at 80℃; for 24h;Inert atmosphere; [00599] To a mixture of copper(I) iodide (0.96 g, 5 mmol), 2-picolinic acid (1.23 g, 10 mmol), iodobenzene (10.2 g, 50 mmol), <strong>[6358-06-1]5-amino-2-chlorophenol</strong> (10.2 g, 70 mmol) and K3PO4 (21.2g, 100 mmol), DMSO (150 mL) was added under nitrogen. The reaction mixture was stirred vigorously for 24 h at 80 C. The reaction mixture was cooled to room temperature. Ethyl acetate (500 mL) and H20 (300 mL) were added. The organic layer was separated and the aqueous layer was extracted twice more with ethyl acetate (200 mL). Combined organic layers were dried over anhydrous Na2S04 and concentrated in vacuo. The crude product was purified by column chromatography (Si02, petrol ether/EtOAc 70:30) to give the title compound 4-chloro-3-phenoxybenzenamine (7.5 g, 34 mmol, 68%) as a white solid. ESI-MS (EI+, m/z): 220.2[M+H]+.
  • 36
  • [ 591-50-4 ]
  • [ 618442-57-2 ]
  • 37
  • [ 2401-21-0 ]
  • [ 82833-74-7 ]
  • [ 591-50-4 ]
  • [ 4323-64-2 ]
  • 38
  • [ 2401-21-0 ]
  • [ 82833-73-6 ]
  • [ 4124-92-9 ]
  • [ 591-50-4 ]
  • 39
  • [ 591-50-4 ]
  • [ 19430-93-4 ]
  • [ 95452-53-2 ]
  • [ 80967-16-4 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; C30H25ClN2P2Pd; In N,N-dimethyl-formamide; at 110℃; for 24h;Sealed tube; General procedure: A sealed tube was charged with aryl halide (1.0 mmol), fluoroalkyl-substituted ethylenes (1.1 mmol), K3PO4 (1.0 mmol), DMF (2 mL) and catalyst (1 molpercent Pd), the mixture was stirred at a certain temperature for a certain time. After being cooled to room temperature, the mixture was filtered. The solvent and excess fluoroalkyl-substituted ethylenes were removed under reduced pressure and the residue was purified by F-SPE technique. Menthol and H2O (v/v = 8:2) were used as fluorophobic elution, while H2O were used as fluorophilic elution. The product was obtained from fluorous phase in high purity.
  • 40
  • [ 14432-12-3 ]
  • [ 591-50-4 ]
  • [ 73183-34-3 ]
  • [ 42260-39-9 ]
  • 41
  • [ 591-50-4 ]
  • [ 63139-21-9 ]
  • [ 5707-44-8 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate; In ethanol; water; at 60℃; for 1h;Green chemistry; General procedure: A mixture of aryl halide (0.125mmol), phenylboronic acid(0.126mmol), K2CO3(0.187mmol), in 0.5ml H2O:EtOH(1:1) and Pd(II)NA2SMNP (0.0006g, 0.02mol%) wasstirred at 60C for the appropriate of time. The progressof the reaction was monitored by TLC. After completionthe reaction, the catalyst was removed with an externalmagnet and washed with EtOH, dried and used directly fora subsequent round of reaction without further purification.Then, desired product (liquid phase) was extracted byplate chromatography eluted with n-hexane/EtOAc (10:1).
94% With C22H28Cl2O4PdS2; caesium carbonate; In ethanol; at 78℃; for 4h; General procedure: A one-pot mixture of aryl halide (0.75 mmol), arylboronic acid(1 mmol), catalyst (0.005 mol%), Cs2CO3 (1.5 mmol) and EtOH(2 ml) was heated to 78 C for 4 h. The reactions progress was monitoredby thin layer chromatography (TLC). After completion of thereaction, the mixture was cooled to room temperature and dilutedwith n-hexane (15 ml) and water (15 ml). The resulting organiclayer was twice washed with brine (15 ml) and dried over CaCl2,filtered and purified by recrystallization or silica gel column chromatography(n-hexane: EtOAc, 80:20) and analyzed by NMR spectroscopy (1H and 13C).
91% With C68H58Cl4Cu2O2P4; caesium carbonate; In N,N-dimethyl-formamide; at 130℃; for 24h;Schlenk technique; Inert atmosphere;Catalytic behavior; General procedure: In a typical run, a 25 ml Schlenk tube was charged with amixture of an aryl halide (0.5 mmol), 4-ethyl phenylboronic acid(0.75 mmol), catalyst (5 mol%), Cs2CO3 (1.5 mmol) and DMF (2 ml)under nitrogen. The tube was placed in a 130 C oil bath and stirredfor 24 h. The reaction progress was monitored by thin-layer chromatography(TLC). The reaction mixture was then cooled to roomtemperature and then 15 ml water was added, followed byextraction with n-hexane (15 ml) The combined organic layer werewashed with brine (3 15 ml) and dried over CaCl2. The solventwas evaporated and a crude product was obtained. The purifiedproducts were identified by comparison of their 1H and 13C NMRspectral data with the literature [33]. Yields were calculated againstconsumption of the aryl halides.
91% With [Ph2PCH2PPh2CH=C(O)(C10H7)]PdCl2}; caesium carbonate; In water; at 80℃; for 0.333333h; General procedure: A reaction tube was charged with the required aryl halide (0.75 mmol), aryl boronic acid (1 mmol), Pd catalyst(0.001 mmol) and Cs2CO3 (1.5 mmol) in water (2 mL). The reaction mixture was stirred for the required period of time at 80 C until completion of the reaction, as monitored by TLC. The final reaction mixture was cooled to room temperature and extracted with n-hexane. The combined organic phase was dried with CaCl2, solvent was removed, and the product was recrystallized from ethanol. Yields were calculated against consumption of the arylhalides, and pure products were identified by FTIR, 1H and 13C NMR spectroscopy and melting point analysis (See supplementary data).
91% With sodium t-butanolate; In water; at 28℃; for 4h;Irradiation;Catalytic behavior; General procedure: Aryl iodide (1 mmol), aryl boronic acid (1.2 mmol), nano Pd/TiO2 (15 mg), H2O-PEG (5 mL, volume ratio of 1:1), NaOC(CH3)3 (3 mmol) were placed in a 10 mL Pyrex round bottom flask. The flask was covered with a rubber stopper. The reaction vessel was stirred at ambient temperature (28 C) under visible light obtained by irradiation of 15 W flexible white LED strips placed on the walls inside the box spirally and the reaction flask was placed in the center of the box (see SM, S1). The temperature of the reaction system was kept at ambient temperature with an air conditioner and a mechanical fan mounted on the box. After completion of the reaction (monitoring by GC), the catalyst was removed by centrifuging and the resulting mixture was extracted with AcOEt (2×10 mL). The organic layers were combined and dried over anhydrous sodium sulfate (Na2SO4) and further concentrated under reduced pressure. The desired product was purified by column chromatography (CC) on silica gel using n-hexane/ethyl acetate (40:1, 20:1).
83% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 6h;Inert atmosphere; A mixture of iodobenzene (4.08 g, 20 mmol), 4-ethylphenylboronic acid (2.25 g, 15 mmol), Pd(PPh3)4 (0.52 g, 0.45 mmol) and K2CO3 (4.2 g, 30 mmol) in 1,4-dioxane (20 mL) and water (20 mL) was stirred at 100 C for 6 h under N2. The mixture was extracted with EtOAc (3 x 10 mL), and the combined organic extracts were then washed with brine and dried over MgSO4. After the solvent was removed in vacuo, the crude product was purified by column chromatography on silica gel with PE as eluent to yield the corresponding product. 4-Ethyl-1,1'-biphenyl (3j)[10], colorless oil, 83% yield, 1H NMR (400 MHz, CDCl3) delta 7.58(d, 2H, J = 8.4 Hz), 7.52 (d, 2H, J = 8.0 Hz), 7.43 (t, 2H, J = 7.2 Hz), 7.30 (m, 3H), 2.70(q, 2H, J = 7.6 Hz), 1.28 (t, 3H, J = 7.6 Hz). 13C NMR (100 MHz, CDCl3) delta 143.6, 141.4,138.9, 129.0, 128.6, 127.3, 127.3, 127.2, 28.8, 15.9. IR (neat) 2965, 1487, 836, 759, 696 cm-1.
81% With triethylamine; In neat (no solvent); at 70℃; for 2h;Sealed tube; Irradiation; General procedure: In a typical reaction, a mixture of aryl halid (0.2mmol),arylboronic acid (0.22 mmol), Et3N(0.4 mmol) and TiO2-AA-Pd nano hybrid (0.15mol%) was added in a10 mL Pyrex test tube and sealed with septum cap. Then thereaction mixture transferred into a reactor chamber and irradiate dunder magnetic stirring using a CFL lamp (philips,wavelength in the range 390-750nm, 40W, 1.1Wm-2) asthe visible light source at 70C for appropriate time. Aftercompletion of the reaction, TiO2-AA-Pd nanohybrid wasextracted by adding of ethanol (5mL) followed by centrifugingand decantation (3 × 5mL ethanol). Then, desired product(liquid phase) was extracted by plate chromatographyeluted with n-hexane/EtOAc (10/2).
61% With potassium carbonate; In water; N,N-dimethyl-formamide; at 80℃; for 4h; General procedure: The aryl halide (0.5 mmol), arylboronic acid (0.75 mmol), Cell-NHC-Pd (0.75 mol%), K2CO3(1 mmol) and DMF:H2O (1:1) (2.5 mL)were successively added into a 25 mL round bottom flask. The mixture was stirred vigorously at 80 C for the varying specific length of time based on each different substrate. After reaction completion, the solid catalyst was filtered off. The filtrate was extracted with ethyl acetate (3 × 5 mL), washed with water and brine three times, and then dried over anhydrous MgSO4. The MgSO4 was then filtered off. After removal of the solvent, the crude product was purified by preparative TLC (eluent: petroleum ether/ethyl acetate, 20/1) to give the desired product and calculate the yield.
93%Spectr. With potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 4h; General procedure: The efficiency of the designed nanocatalyst was verified in Suzuki cross-coupling reactions. General procedure for catalytic test using the nanocatalyst is as follows. Solvent dimethylformamide (DMF)/H2O (3:1), aryl halide (0.5 mmol),aryl boronic acid (0.6 mmol), K2CO3 (2 mmol), nanocatalyst(1 mol %), and a small stirring bar were added to a round bottom flask (25 mL). The flask containing reaction mixture was placed in an oil bath (100 C) and stirred under air atmosphere. After completion of reaction, the mixture was cooled to room temperature and the nanocatalyst was separated using a magnet. The separated nanocatalyst was washed several times with DMF. Finally the products wer eanalyzed by a gas chromatography mass spectrometer (GCMS).
93%Chromat. With potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 1.5h; General procedure: Nanocomposite Pd catalyst (1 mol%) was added to a round-bottom flask (25 ml) and dispersed in dimethylformamide(DMF)/H2O (2:1) mixture. Then, aryl halide (0.5 mmol), aryl boronic acid (0.6 mmol), K2CO3(1.5 mmol), and a small stirring bar wereadded to the round-bottom flask. The flask containing reaction mixture was placed in an oil bath (100C) and stirred under airatmosphere. After completion of reaction, the mixture was cooled to room temperature and the nanocomposite Pd catalyst was separated using a magnet. The separated catalysts were washed severaltimes with DMF. Finally the products were analyzed by a GC-MS.

  • 42
  • [ 591-50-4 ]
  • [ 172732-52-4 ]
  • [ 24973-49-7 ]
  • 43
  • [ 591-50-4 ]
  • [ 1092351-82-0 ]
  • methyl 1-methyl-3-phenyl-1H-indazole-5-carboxylate [ No CAS ]
  • 44
  • [ 591-50-4 ]
  • [ 19337-60-1 ]
  • 45
  • [ 591-50-4 ]
  • [ 35779-04-5 ]
  • [ 2923-16-2 ]
  • [ 160001-85-4 ]
  • [ 98-08-8 ]
  • 46
  • [ 591-50-4 ]
  • [ 696-62-8 ]
  • [ 2923-16-2 ]
  • [ 98-08-8 ]
  • [ 402-52-8 ]
  • 47
  • [ 591-50-4 ]
  • [ 51934-41-9 ]
  • [ 2923-16-2 ]
  • [ 98-08-8 ]
  • [ 583-02-8 ]
  • 48
  • [ 19090-04-1 ]
  • [ 591-50-4 ]
  • [ 20760-17-2 ]
  • 49
  • [ 591-50-4 ]
  • [ 1001-26-9 ]
  • (Z)-3-Ethoxy-3-phenyl-acrylic acid ethyl ester [ No CAS ]
  • 50
  • [ 591-50-4 ]
  • [ 6336-32-9 ]
  • [ 1316311-27-9 ]
YieldReaction ConditionsOperation in experiment
26% With potassium phosphate; copper(l) iodide; trans-1,2-cyclohexanediamine; In 1,4-dioxane; for 48h;Inert atmosphere; Reflux; In an argon atmosphere, 50 ml of dehydrated 1,4-dioxane was added to a mixture of 5.1 g (20.0 mmol) of intermediate 2-2, 4.1 g (20.0 mmol) of iodobenzene, 3.8 g (20.0 mmol) of copper iodide, 6.9 g (60.0 mmol) of trans-1,2-cyclohexanediamine, and 12.7 g (60.0 mmol) of tripotassium phosphste. The resultant mixture was stirred for 48 h while refluxing under heating. The reaction solution was concentrated under reduced pressure. The obtained residue was added with 1000 ml of toluene, heated to 120 °C, and then filtered to remove the insolubles. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography, to obtain 1.7 g of brown solid, which was identified as the following intermediate 2-3 by FD-MS analysis (yield: 26percent).
  • 52
  • [ 591-50-4 ]
  • [ 19616-28-5 ]
  • [ 159946-78-8 ]
YieldReaction ConditionsOperation in experiment
98.6% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; at 120℃; for 16h;Inert atmosphere; [136] N-(2,4-dimethylphenyl)-2,4-dimethyl-N-phenylaniline (Compound 15): A mixture of <strong>[19616-28-5]bis(2,4-dimethylphenyl)amine</strong> (Compound 14) (9.4 g, 41 .8 mmol), iodobenzene (17.14 g, 84 mmol), Pd(OAc)2 (0.47 g, 2.1 mmol), P(t-Bu)3 (0.848 g, 4.2 mmol), sodium tert-butoxide (7.68 g, 80 mmol) in toluene (120 mL) was degassed and heated at 120°C for 16 hours. The resulting mixture was poured into ethyl acetate (250 mL), washed with brine, dried over Na2S04, loaded on silicagel and purified by flash column using eluent of hexanes. After removal of solvent, an oil (Compound 15) was obtained (12.4 g, in 98.6percent yield).
  • 53
  • [ 591-50-4 ]
  • [ 119072-55-8 ]
  • [ 5900-59-4 ]
  • [ 7012-94-4 ]
  • 54
  • [ 591-50-4 ]
  • [ 1092351-82-0 ]
  • methyl 1-methyl-3-phenyl-1H-indazole-5-carboxylate [ No CAS ]
  • [ 1620816-71-8 ]
  • 55
  • [ 591-50-4 ]
  • C8H7ClMgN2 [ No CAS ]
  • [ 2622-63-1 ]
  • 56
  • [ 1075-34-9 ]
  • [ 591-50-4 ]
  • [ 1069051-37-1 ]
  • 57
  • [ 591-50-4 ]
  • [ 162607-20-7 ]
  • [ 5069-26-1 ]
  • 58
  • [ 591-50-4 ]
  • [ 73819-76-8 ]
  • [ 119389-05-8 ]
  • 59
  • [ 52522-40-4 ]
  • [ 591-50-4 ]
  • [ 161265-03-8 ]
  • [(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)palladium(II)(phenyl)iodine] [ No CAS ]
  • 62
  • [ 2460-58-4 ]
  • [ 591-50-4 ]
  • [ 1834-88-4 ]
  • 63
  • [ 591-50-4 ]
  • [ 5744-68-3 ]
  • [ 41327-15-5 ]
YieldReaction ConditionsOperation in experiment
87% (1) Preparation of Compound IIIa: Compound IV (160g, 1mol) was added to 900ml of tetrahydrofuran,Was slowly added portionwise sodium tert-butoxide (115.2g, 1.2mol), stirred for 20 minutes, a solution of iodine benzene (243.6g, 1.2mol). The mixture was heated at reflux for 4 hours with stirring, and then stirred at room temperature overnight, TLC showed the reaction was complete, the reaction mixture was slowly poured into ice water, ethyl acetate was added, the organic phase was separated, the aqueous phase was again extracted with ethyl acetate, the organic phases combined, dried and concentrated to give compound IIIa205.3g, a yield of 87percent.
With pyridine; In acetonitrile; Compound IV was run in acetonitrile, pyridine,With the compound iodobenzene nucleophilic substitution reaction preparation of compound III,
  • 64
  • [ 285-69-8 ]
  • [ 591-50-4 ]
  • 3-hydroxy 4-phenylselenotetrahydrofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
84.9% With selenium; potassium phosphate; copper(l) chloride; In dimethyl sulfoxide; at 20 - 130℃; for 29h;Inert atmosphere; Example 10: At room temperature, the reaction vessel in an organic solvent DMSO was added the above formula (II) compound, the compound of formula (III), elemental Se, CuCl and K3PO4.Wherein the molar ratio of the compound of formula (II) and the formula (III) is 1: 1.2, the compound with elemental Se molar ratio of formula (II) is 1: 2.8, the molar amount of CuCl is of formula (II) compound molar amount 25 percent, with a compound of formula (II) K3PO4The molar ratio of 1: 0.9, and then purged with nitrogen, and replaced twice, in a nitrogen atmosphere such that the reaction environment; was warmed to 130 , and incubated for 29 hours the reaction.After post-treatment to give the product of formula (the I), in a yield of 84.9percent, purity 98.3percent (HPLC).
  • 65
  • [ 1123-93-9 ]
  • [ 591-50-4 ]
  • 5-amino-2-phenylselenobenzothiazole [ No CAS ]
  • 66
  • [ 591-50-4 ]
  • [ 54624-57-6 ]
  • 2-bromo-1-phenyl-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With copper(l) iodide; 18-crown-6 ether; potassium carbonate; In N,N-dimethyl acetamide; at 165℃; for 12h;Inert atmosphere; In a 500 mL three-necked flask, <strong>[54624-57-6]<strong>[54624-57-6]2-bromo-1H-benzimidazol</strong>e</strong> (39.41 g, 200 mmol), iodobenzene (40.79 g, 200 mmol), crown ether (5.29 g, 20 mmol), potassium carbonate (82.92 g, 600 mmol), Dimethylacetamide (200 g), under the protection of nitrogen, continued addition of cuprous iodide (3.81 g, 20 mmol), the temperature was raised to 165 C, and the reaction was carried out for 12 h. The reaction was monitored by HPLC and the reaction was stopped. The mixture was washed with water, filtered, and ethanol-purified to give intermediate a0: 2-bromo-1-phenyl-1H-benzimidazole 47.52 g, yield 87%.
78.5% With copper(l) iodide; 1,10-Phenanthroline; sodium hydride;Inert atmosphere; (1) In a 250 mL three-necked flask, nitrogen gas was introduced, and 0.02 mol of the raw material B1, 0.03 mol of the raw material E1, 0.04 mol of sodium hydride,0.004 mol of cuprous iodide and 0.01 mol of phenanthroline are dissolved in 100 ml of 1,3-dimethyl-2-imidazolidinone, and the reaction is stirred for 20-30 h.After the reaction, water was added and the mixture was extracted with dichloromethane.The mixture was washed with a mixture of petroleum ether and ethyl acetate, and the volume ratio of petroleum ether to ethyl acetate in the eluent was 1:100.Purification by column chromatography gave Intermediate X1; HPLC purity: 99.7%, yield 78.5%.
75.8% With 1,3-dimethyl-2-imidazolidinone; copper(l) iodide; 1,10-Phenanthroline; sodium hydride;Inert atmosphere; In a 250 mL three-necked flask,Access to nitrogen,0.02 mol of the starting material <strong>[54624-57-6]<strong>[54624-57-6]2-bromo-1H-benzimidazol</strong>e</strong> was added,0.03 mol of iodobenzene,0.04 mol of sodium hydride,0.004 mol of cuprous iodide and 0.01 mol of phenanthroline were dissolved in 100 ml of 1,3-dimethyl-2-imidazolidinone,Stirring reaction 20-30h,After the reaction,Add water and extract with methylene chloride,The organic layer was dried over anhydrous sodium sulfate,With a mixture of petroleum ether and ethyl acetate as eluent leaching,The volume ratio of petroleum ether to ethyl acetate in the eluent was 1: 100,Column chromatography to give Intermediate M1; HPLC purity 99.5%, yield 75.8%.
75.8% With copper(l) iodide; 1,10-Phenanthroline; sodium hydride;Inert atmosphere; (1) in 250mL three-necked flask,Purged with nitrogen,0.02mol raw material <strong>[54624-57-6]<strong>[54624-57-6]2-bromo-1H-benzimidazol</strong>e</strong> was added,0.03mol iodobenzene,0.04 mol sodium hydride, 0.004 mol copper iodideAnd 0.01 mol of o-phenanthroline were dissolved in 100 ml of 1,3-dimethyl-2-imidazolidinone,The reaction was stirred for 20-30h,After the reaction was completed, water was added and the mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and rinsed with a mixture of petroleum ether and ethyl acetate. The volume ratio of petroleum ether to ethyl acetate in the eluent was 1 : 100, purified by column chromatography to give Intermediate M1;HPLC purity 99.5%, yield 75.8%.
75.8% With 1,3-dimethyl-2-imidazolidinone; copper(l) iodide; 1,10-Phenanthroline; sodium hydride;Inert atmosphere; (1) In a 250mL three-necked flask, purged with nitrogen, 0.02mol raw material <strong>[54624-57-6]<strong>[54624-57-6]2-bromo-1H-benzimidazol</strong>e</strong>, 0.03mol iodobenzene, 0.04mol sodium hydride,0.004mol cuprous iodide and 0.01mol o-phenanthroline dissolved in 100ml 1,3-dimethyl-2-imidazolidinone, the reaction was stirred for 20-30h,After the reaction was completed, water was added and the mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate,A mixture of petroleum ether and ethyl acetate was used as a eluent shower, the volume ratio of petroleum ether to ethyl acetate in the eluent was 1: 100,Purification by column chromatography gave Intermediate M1; HPLC purity 99.5%, yield 75.8%.

  • 67
  • [ 591-50-4 ]
  • [ 6825-20-3 ]
  • [ 4043-87-2 ]
  • [ 57103-20-5 ]
YieldReaction ConditionsOperation in experiment
90.5% With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 110℃; for 12h;Inert atmosphere; A.3,6-dibromocarbazole (200 mg, 0.62 mmol) was dissolved in DMF solvent,Then iodobenzene (188.3 mg, 0.92 mmol) was added,DL-piperidinecarboxylic acid (11.88 mg, 0.09 mmol),Cuprous oxide (8.27 mg, 0.04 mmol),Cesium carbonate (299.75 mg, 0.92 mmol),Under nitrogen protection,The reaction system was placed at 110 ° C under reflux for 12 h,After the reaction is complete,Ethyl acetate extraction,Organic layer washed three times,Dried over anhydrous sodium sulfate,The solvent is evaporated under reduced pressure;The crude product was purified by column chromatography with ethyl acetate and petroleum ether mixed solvent (20: 1)To obtain compound 3,6-dibromo-9-phenylcarbazole (white solid, 225 mg, yield 90.5percent).
  • 69
  • [ 591-50-4 ]
  • [ 33209-01-7 ]
  • (2S,3R)-2-amino-3-hydroxy-N-phenylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With 15-crown-5; caesium carbonate; copper(l) chloride; N,N`-dimethylethylenediamine; In toluene; at 110℃; for 18h;Schlenk technique; Sealed tube; Inert atmosphere; General procedure: A 25-mL of Schlenk-type tube equipped with a magnetic stir bar was charged with a chiral amino acid amide or its hydrochloride (1.2 mmol), Cs2CO3 (2.0 mmol; 3.0 mmol used when amino acid amide hydrochloride was used), and CuCl (0.1mmol) before sealing. A syringe was used under a nitrogen atmosphere to add aryl halide (1.0mmol), DMEDA (1.0 mmol), toluene (4.0 mL) and 15-Crown-5 (0.2mmol). The tube was put into an oil bath pot preheated at 110°C and was stirred at a steady temperature for 18 h. The reaction mixture was then cooled to room temperature, quenched with water, and extracted with ethyl acetate (20 mL) for three times. The organic layers were combined, dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with a solution of dichloromethane and ethyl alcohol (80/1 to 10/1) to afford the chiral alpha-amino anilides.
  • 70
  • [ 591-50-4 ]
  • [ 4532-33-6 ]
  • 71
  • [ 591-50-4 ]
  • [ 201230-82-2 ]
  • [ 39549-79-6 ]
  • 7-methyl-2-phenylquinazoline-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 120℃; under 7500.75 Torr; for 20h;Inert atmosphere; Autoclave; General procedure: A 12mL vial was charged with MCM-41-2P-Pd(OAc)2 (2mol%), 2-aminobenzamide (1mmol), aryl iodide (1mmol) (if solid) and a stirring bar. Then, DMF (2mL), aryl iodide (1mmol) (if liquid) and DBU (2mmol) were injected by syringe under an argon atmosphere. The vial was placed in an alloy plate, which was transferred into a 300mL Parr Instruments 4560 series autoclave under an argon atmosphere. After flushing the autoclave three times with CO, a pressure of 10bar CO was fixed at ambient temperature. The autoclave was heated for 20hat 120C. After completion of the reaction, the autoclave was cooled to room temperature and the pressure was released carefully. The reaction mixture was diluted with ethyl acetate (10mL) and filtered. The palladium catalyst was washed with distilled water (2×5mL) and acetone (2×5mL), and reused in the next run. The filtrate was concentrated in vacuo and the pure product was isolated by either washed with water, ethyl acetate and finally hexane or recrystallization from MeOH.
  • 72
  • [ 591-50-4 ]
  • [ 201230-82-2 ]
  • [ 31930-18-4 ]
  • [ 26059-83-6 ]
YieldReaction ConditionsOperation in experiment
73% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 120℃; under 7500.75 Torr; for 20h;Inert atmosphere; Autoclave; General procedure: A 12mL vial was charged with MCM-41-2P-Pd(OAc)2 (2molpercent), 2-aminobenzamide (1mmol), aryl iodide (1mmol) (if solid) and a stirring bar. Then, DMF (2mL), aryl iodide (1mmol) (if liquid) and DBU (2mmol) were injected by syringe under an argon atmosphere. The vial was placed in an alloy plate, which was transferred into a 300mL Parr Instruments 4560 series autoclave under an argon atmosphere. After flushing the autoclave three times with CO, a pressure of 10bar CO was fixed at ambient temperature. The autoclave was heated for 20hat 120°C. After completion of the reaction, the autoclave was cooled to room temperature and the pressure was released carefully. The reaction mixture was diluted with ethyl acetate (10mL) and filtered. The palladium catalyst was washed with distilled water (2×5mL) and acetone (2×5mL), and reused in the next run. The filtrate was concentrated in vacuo and the pure product was isolated by either washed with water, ethyl acetate and finally hexane or recrystallization from MeOH.
  • 73
  • [ 591-50-4 ]
  • [ 57297-29-7 ]
  • [ 1342132-54-0 ]
  • 74
  • [ 591-50-4 ]
  • [ 6358-06-1 ]
  • tert-butyl 4-chloro-3-phenoxyphenylcarbamate [ No CAS ]
  • 75
  • [ 591-50-4 ]
  • [ 272-52-6 ]
  • 3-phenyl-1H-pyrazolo[4,3-b]pyridine [ No CAS ]
  • 76
  • [ 591-50-4 ]
  • [ 6638-05-7 ]
  • 2,6-dimethoxy-4-methylphenoxybenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 2-Picolinic acid; potassium phosphate; copper(l) iodide; In dimethyl sulfoxide; at 100℃; for 20.0h;Schlenk technique; Inert atmosphere; General procedure: A round-bottom Schlenk-flask (250 mL) was equipped with a magnetic stir bar, copperiodide (456 mg,2.40 mmol, 10.0 molpercent), picolinic acid (590 mg, 4.80 mmol, 20.0 molpercent) and potassium phosphate(10.2 g, 48.0 mmol, 2.00 eq.). A second Schlenk flask (100 mL) was charged with the aryliodide(24.0 mmol, 1 eq.), the phenol (28.8 mmol, 1.2 eq.) and anhydrous DMSO (50 mL). The solution offlask 2 was transferred into flask 1 under flowing Argon and the reaction mixture was stirred for 20 h at100 °C, subsequently. After cooling down, the reaction mixture was diluted with a 1:1 mixture of asaturated aqueous solution of NH4Cl (200 mL) and H2O (200 mL). After extraction with DCM(3· 200 mL) the combined organic phases were washed with a 5percent aqueous solution of KOH (300 mL)and brine (300 mL). After drying the mixture over Na2SO4 the solvent was removed and the crudereaction mixture was preadsorbed on silica gel. The purification of the crude mixture was achieved oversilica gel, respectively. Remaining iodine compounds caused the deactivation of the catalyst insubsequent catalysis reactions and therefore had to be separated carefully. This afforded in some casesa purification by two subsequent chromatography columns.
  • 78
  • [ 10241-97-1 ]
  • [ 591-50-4 ]
  • 5-methyl-1-phenyl-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With copper(I) oxide; potassium phosphate; In 1-methyl-pyrrolidin-2-one; at 160℃; for 12h;Inert atmosphere; Schlenk technique; General procedure: A mixture of Cu2O (0.02 mmol), K3PO4 (0.4 mmol), indole-2-carboxylic acid (1) (0.2 mmol), and aryl halide (2) (0.2 mmol) in NMP (2.0 mL) was stirred at room temperature under a N2 atmosphere. The mixture was then heated to 160 °C and stirred at this temperature for 12 h. After completion of the reaction, the mixture was cooled to room temperature and diluted with EtOAc. The mixture was washed with H2O and aq NaCl, dried over MgSO4 and filtered. After evaporation of the solvent, the residue was purified by preparative thin-layer chromatography on silica gel with PE/EtOAc (50:1) as eluent to give the product 3.
  • 79
  • [ 591-50-4 ]
  • [ 5779-93-1 ]
  • [ 610-48-0 ]
YieldReaction ConditionsOperation in experiment
46% With trifluorormethanesulfonic acid; palladium diacetate; silver trifluoroacetate; acetic acid; glycine; at 100℃; for 24h;Sealed tube; General procedure: A sealed tube with magnetic stir bar was charged with substrate 1 (0.24 mmol), glycine (0.1 mmol, 7.5 mg), Pd(OAc)2 (0.02 mmol, 4.45 mg), AgTFA (0.24 mmol, 53.01 mg) and 2 (0.2 mmol) under air. After addition of AcOH (2 mL) as solvent, TfOH (0.1 mmol, 15.0 mg) was added. The reaction mixture was allowed to stir at 100 C for 24 hours. Upon completion, the reaction mixture was cooled to room temperature, diluted with DCM, and then extracted with saturated NaHCO3 aqueous solution. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel using PE as the eluent to afford the desired products.
  • 80
  • [ 591-50-4 ]
  • [ 3469-20-3 ]
  • [ 54879-94-6 ]
YieldReaction ConditionsOperation in experiment
70% With sodium t-butanolate; In dimethyl sulfoxide; at 120℃; for 12h; General procedure: 2-Phenylindole (408 mg, 2.0 mmol, 1 equiv), aryl iodide (2.0 mmol, 1 equiv), NaOt-Bu (288mg, 3.0 mmol,, 1.5 equiv), CNT-CuO (contained Cu 9.1 %, 70 mg, 5.0 mol%), were reacted in DMSO (10.0 mL) at 120 C for 12 h. The mixture charged to separating funnel added water, extracted with EtOAc. The organic layer washed with water many times for removing water, dried over magnesium sulfate. Evaporation of the solvent under reduced pressure provided the crude product, which was purified by column chromatography on silica gel.(eluent : hexane / ethyl acetate = 10 / 1).
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[ 591-50-4 ]

Chemical Structure| 104130-35-0

A1462804[ 104130-35-0 ]

Iodobenzene-13C6

Reason: Stable Isotope