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[ CAS No. 68716-52-9 ] {[proInfo.proName]}

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Chemical Structure| 68716-52-9
Chemical Structure| 68716-52-9
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Product Details of [ 68716-52-9 ]

CAS No. :68716-52-9 MDL No. :MFCD05663869
Formula : C16H19BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WQGRAXGAXSNSDL-UHFFFAOYSA-N
M.W : 254.13 Pubchem ID :2760174
Synonyms :

Safety of [ 68716-52-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 68716-52-9 ]

* 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 [ 68716-52-9 ]

[ 68716-52-9 ] Synthesis Path-Downstream   1~87

  • 1
  • [ 90-11-9 ]
  • [ 25015-63-8 ]
  • [ 68716-52-9 ]
  • 3
  • [ 106-37-6 ]
  • [ 68716-52-9 ]
  • [ 605-02-7 ]
  • [ 64065-97-0 ]
  • 4
  • [ 68716-52-9 ]
  • [ 207612-71-3 ]
  • 4,4'-bis(1-naphthyl)-1,1'-biphenyl [ No CAS ]
  • 5
  • [ 90-11-9 ]
  • [ 25015-63-8 ]
  • [ 91-20-3 ]
  • [ 68716-52-9 ]
  • 6
  • [ 99747-74-7 ]
  • [ 25015-63-8 ]
  • [ 91-20-3 ]
  • [ 68716-52-9 ]
  • 7
  • [ 76-09-5 ]
  • [ 90-14-2 ]
  • [ 91-20-3 ]
  • [ 68716-52-9 ]
  • 8
  • [ 68716-52-9 ]
  • 5-Bromo-6,8-dimethoxy-trans-1,3-dimethylisochromane [ No CAS ]
  • 6,8-Dimethoxy-trans-1,3-dimethylisochroman [ No CAS ]
  • 6,7-Dimethoxy-trans-1,3-dimethyl-5-(1-naphthyl)isochromane [ No CAS ]
  • 10
  • [ 105-36-2 ]
  • [ 68716-52-9 ]
  • [ 2122-70-5 ]
  • 11
  • [ 141-12-8 ]
  • [ 68716-52-9 ]
  • 1-((Z)-3,7-Dimethyl-octa-2,6-dienyl)-naphthalene [ No CAS ]
  • (E)-1-(3,7-dimethylocta-2,6-dienyl)naphthalene [ No CAS ]
  • 12
  • [ 105-87-3 ]
  • [ 68716-52-9 ]
  • 1-((Z)-3,7-Dimethyl-octa-2,6-dienyl)-naphthalene [ No CAS ]
  • (E)-1-(3,7-dimethylocta-2,6-dienyl)naphthalene [ No CAS ]
  • 13
  • [ 21040-45-9 ]
  • [ 68716-52-9 ]
  • [ 5751-29-1 ]
  • 14
  • [ 25240-59-9 ]
  • [ 99747-74-7 ]
  • [ 68716-52-9 ]
  • 15
  • [ 68716-52-9 ]
  • [ 90-11-9 ]
  • 18
  • [ 75-09-2 ]
  • [ 108-24-7 ]
  • [ 68716-52-9 ]
  • [ 867182-10-3 ]
  • 19
  • 6-bromo-6'-[(R)-2,2'-dimethoxy-1,1'-binaphthyl-6-]-2,2'-bipyridine [ No CAS ]
  • [ 68716-52-9 ]
  • 6-[(R)-2,2'-dimethoxy-1,1'-binaphthyl-6-]-6'-(1-naphthyl)-2,2'-bipyridine [ No CAS ]
  • 20
  • [ 90-14-2 ]
  • [ 25015-63-8 ]
  • [ 68716-52-9 ]
  • 21
  • [ 18013-97-3 ]
  • [ 68716-52-9 ]
  • [ 913175-30-1 ]
  • 22
  • [ 1005495-05-5 ]
  • [ 1005495-06-6 ]
  • [ 68716-52-9 ]
  • C41H25N [ No CAS ]
  • C41H25N [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 2h;Heating / reflux; <Example 5> [Method of producing Exemplified Compound No. 1540]; <n="155"/> <n="156"/>Under a nitrogen atmosphere, 0.50 g (1.03 iraalphaol) of the mixture of Intermediate Compounds 4 and 5, 0.19 g (1.10 mmol) of 4, 4, 5, 5-tetramethyl-2- (naphthalen-1- - yl) -1, 3, 2-dioxaborolane, and 0.06 g (0.05 mmol) of tetrakistriphenylphosphinepalladium were suspended in a mixed solvent of 25 mL of toluene, 13 mL of ethanol, and 10 mL of a 10% aqueous solution of sodium carbonate. The resultant solution was stirred under heat and ? reflux for 2 hours, and the disappearance of Intermediate Compounds 4 and 5 was observed. After that, the resultant was cooled to room temperature, and water was added to the resultant to stop the reaction. An organic layer, was separated, and was then washed with water twice. After that, the solvent was removed by distillation. The resultant residue was purified by- silica gel column chromatography (toluene : ethyl acetate = 10 : 1), whereby 0.47betag of the mixture of Exemplified Compounds 1540 containing Exemplified Compounds 1540-1 and 1540-2 at a composition ratio of 1 : 1 was obtained.NMR measurement identified the structure, of the compound (FIG. 10) .The PL spectrum of a solution (1.0 x lO"5 mol/L) of Exemplified Compound 1540 in toluene was measured. As a result, a blue light emission spectrum having a light emission peak at 434 nm, a half width of 62 nm, and an excellent color purity was shown (FIG. 16) .
  • 23
  • [ 1011472-05-1 ]
  • [ 68716-52-9 ]
  • [ 1011472-06-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 160℃; for 0.166667h;Microwave irradiation; to a solution of LG2-87 (25 mg, 0.076 mmol), 2-(l- naphthylene)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (39 mg, 0.152 mmol, 2.0 equiv.), and Tetrakis(triphenylphosphine)-palladium(0) (11 mg, 0.0096 mmol) in THF (1.0 ml) was added 0.5 ml of aqueous 1 N K2CO3 solution. The resultant mixture was heated at 160 0C under microwave irradiation for 10 min. The mixture was diluted with EtOAc (10 ml), and the organic phase was separated out. After removal of solvent, the residue was subjected to flash column chromatography on silica gel (elution with hexane-EtOAc) to yield LG2-89 as a white foam (33 mg). ESI-MS: m/z 376 (M+l); IH NMR (600 MHz, CDC13): delta 8.23 (IH, s), 8.18 (IH, br .s), 8.11 (IH, s), 8.02 (IH, br. s), 7.98 (IH, d, J= 7.8 Hz), 7.73 (IH, s), 7.62 (3H, m), 7.57 (IH, t, J= 7.2 Hz), 7.52 (IH, d, J= 8.4 Hz), 7.49 (IH, t, J= 7.8 Hz), 7.42 (IH, d, J= 9.0 Hz), 7.39 (IH, d, J= 4.2 Hz), 7.23 (IH, s), 7.13 (IH, d, J= 4.2 Hz), 6.59 (IH, s); 13C NMR (150.9 MHz, CDC13): delta 147.36, 133.91, 133.84, 132.91, 132.22, 131.98, 131.78,HOU03:1125151 <n="23"/>129.94, 129.10, 128.70, 128.63, 128.32, 127.13, 126.58, 126.51, 125.61, 125.49, 125.20, 124.93, 117.03, 112.68, 111.27, 109.27, 103.01.
  • 24
  • [ 3240-34-4 ]
  • [ 68716-52-9 ]
  • naphthalen-1-yl(phenyl)iodonium tetrafluoroborate [ No CAS ]
  • 25
  • [ 68716-52-9 ]
  • [ 867182-02-3 ]
  • 26
  • [ 68716-52-9 ]
  • <i>N</i>-[(4-methyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-1-yl-methyl]-acetamide [ No CAS ]
  • 27
  • [ 68716-52-9 ]
  • <i>N</i>-[(4-<i>tert</i>-butyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-1-yl-methyl]-acetamide [ No CAS ]
  • 28
  • [ 68716-52-9 ]
  • (S)-3,3'-di[2-(6-(1-naphthyl)pyridyl)]-2,2'-dihydroxy-1,1'-binaphthyl [ No CAS ]
  • 29
  • [ 68716-52-9 ]
  • C54H40N2O4 [ No CAS ]
  • 31
  • [ 90-11-9 ]
  • [ 73183-34-3 ]
  • [ 68716-52-9 ]
YieldReaction ConditionsOperation in experiment
92.7% With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In tetrahydrofuran; at 80℃; for 5h;Inert atmosphere; In a 250 mL three-necked flask, nitrogen gas is introduced.Add 0.02 mol of 1-bromonaphthalene dissolved in 100 ml of tetrahydrofuran (THF), and then add 0.024 mol of bis(pinacolyl)diboron, 0.0002 mol of (1,1'-bis(diphenylphosphino)ferrocene) dichloride. Palladium (II) and 0.05 mol of potassium acetate were added, the mixture was stirred, and the mixed solution of the above reactants was heated and refluxed at a reaction temperature of 80 C for 5 hours; after the reaction was completed, 100 ml of water was added thereto, and the mixture was filtered and dried in a vacuum oven. Dry in the middle. The obtained residue was separated and purified on a silica gel column to obtain 4-biphenylboronic acid pinacol ester; HPLC purity: 99.9%, yield: 92.7%.
74% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 120℃; for 12h; 1-bromonaphthalene (50.0 g, 241 mmol), bis (pinacolato) diboron (67.4 g, 266 mmol), KOAc (71 g, 724 mmol),PdCl 2 (dppf) (5.30 g, 7.24 mmol) was dissolved in DMF (1 L) solvent, and refluxed at 120 C. for 12 hours.When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH2Cl2, and wiped with water.After drying and concentrating the organic layer with MgSO4, the resulting organic material was used with CH2Cl2 and methanol solvent.Recrystallization gave 45.4 g (yield: 74%) of the desired product.
73% With tetrakis(triphenylphosphine) palladium(0); potassium acetate; In toluene; for 24h; Sub B (1)-2 (4.14g, 20mmol) was dissolved in 48 mL toluene, bis(pinacolato)diboron (5.58g, 22mmol), Pd (dppf) Cl2 catalyst (0.44g, 0.6mmol), KOAc (5.89 g, was added as 60mmol) the sequence after 24 hours with stirring to synthesize a borate compound, and then the resulting compound was separated through a silica gel column and recrystallized to obtain 3.7g to Sub B-2. (Yield: 73%)
57% With potassium acetate;[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; In dimethyl sulfoxide; at 90℃; for 42h;Product distribution / selectivity; In air, a vial was charged with Ih (10.2 mg, 0.015 mmol, 3 mol %), bis(pinacolato)diboron (0.1397 g, 0.55 mmol) and KOAc (0.147 g, 1.5 mmol). The vial was sealed and purged with argon. Bromobenzene (52 muL, 0.5 mmol) and 3 mL of DMSO were then added. The resulting mixture was then stirred at 90 C. until the reaction was complete. The product was extracted into ether, separated and dried over MgSO4. The product was purified by column chromatography. Results for various substrate scope and reaction conditions are presented in Table 9.

  • 33
  • [ 61676-62-8 ]
  • [ 90-11-9 ]
  • [ 68716-52-9 ]
YieldReaction ConditionsOperation in experiment
77% 1-bromo- naphthalene 2.07 g (10 mmol) was dissolved in 30 mL THF , 4 mL of n -butyllithium at -78 ( 2.5M inHexane) was added. After an hour at the same temperature, 22-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2.0 mL (10 mmol) was added . After stirring for 5 hours at room temperature water was added and three times with diethyl ether (30 mL)Washed . After drying the washed diethyl ether layer over MgSO4 followed by drying under reduced pressure the product was obtained and then purified by silica gel columnPurification by intermediate I-1 1.96 g ( yield 77 %) was obtained by chromatography . And the resulting compound is confirmed by LC-MS
77% 1-bromo-naphthalene 2.07 g (10 mmol) to 30 mL THF and then dissolved, n-butyl lithium at -78C mL 4 (2.5M in Hexane) was added. After an hour at the same temperature, 2-isopropoxy-4,4,5,5-tetramethyl-1, 3,2-dioxaborolane(2-isopropoxy-4,4,5,5-tetramethyl-1, 3,2-dioxaborolane) 2.0 mL (10 mmol) was added. After stirring for 5 hours at room temperature water was added and washed three times with diethyl ether (30 mL). After drying the washed diethyl ether layer over MgSO4 dried under reduced pressure to obtain a product, followed by separation by silica gel column chromatography purification Intermediate I-9 1.96 g (yield 77%). The resulting compound was confirmed by LC-MS.
  • 34
  • [ 90-14-2 ]
  • [ 73183-34-3 ]
  • [ 94647-81-1 ]
  • [ 68716-52-9 ]
  • 35
  • [ 90-14-2 ]
  • [ 73183-34-3 ]
  • [ 68716-52-9 ]
YieldReaction ConditionsOperation in experiment
32%Chromat. With copper(II) ferrite; potassium tert-butylate; In N,N-dimethyl-formamide; at 20℃; for 12h;Green chemistry; General procedure: 4-Iodoanisole (0.813 mmol, 200 mg), bis(pinacolato)diboron (1.219 mmol, 309 mg) were dissolved in 3 mL of dmf followed by copper ferrite nanoparticles (5mol% with respect to 4-iodoanisole) and potassiumtert-butoxide (1.219 mmol, 137 mg) were added to a 10 mLcapped vial and stirred at RT for time indicated. After stirring, the mixture was diluted with diethyl ether and filtered through celite bed. The filtrate was extracted with water (3 times) and the organic phase was dried over anhydrous MgSO4. The crude product was subjected to analyze by GC-MS. The conversion yield is accurately measured based on the consumption of 4-iodoanisole and the side product formed due to protodeiodination.
  • 36
  • [ 91-20-3 ]
  • [ 73183-34-3 ]
  • [ 68716-52-9 ]
  • 37
  • [ 215313-78-3 ]
  • [ 68716-52-9 ]
  • [ 1352088-67-5 ]
  • 38
  • [ 68716-52-9 ]
  • potassium trimethoxy(trifluoromethyl)boranuide [ No CAS ]
  • [ 91-20-3 ]
  • [ 604-53-5 ]
  • [ 26458-04-8 ]
  • [ 2216-69-5 ]
  • 39
  • [ 68716-52-9 ]
  • potassium trimethoxy(trifluoromethyl)boranuide [ No CAS ]
  • [ 604-53-5 ]
  • [ 26458-04-8 ]
  • [ 2216-69-5 ]
  • 40
  • [ 68716-52-9 ]
  • potassium trimethoxy(trifluoromethyl)boranuide [ No CAS ]
  • [ 26458-04-8 ]
  • 41
  • [ 68716-52-9 ]
  • potassium trimethoxy(trifluoromethyl)boranuide [ No CAS ]
  • [ 26458-04-8 ]
  • [ 2216-69-5 ]
  • 42
  • [ 68716-52-9 ]
  • potassium (trifluoromethyl)triethoxyborate [ No CAS ]
  • [ 5328-01-8 ]
  • [ 26458-04-8 ]
  • 43
  • [ 68-12-2 ]
  • [ 68716-52-9 ]
  • [ 86-53-3 ]
  • 44
  • [ 1384579-32-1 ]
  • [ 68716-52-9 ]
  • [ 1384579-38-7 ]
YieldReaction ConditionsOperation in experiment
26% With 1,8-diazabicyclo[5.4.0]undec-7-ene;bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine; In N,N-dimethyl-formamide; at 150℃; for 4h; (3) Synthesis of exemplified compound XX- 1Reagents and a solvent described below were placed in a reactor .Compound X5 : 1.0 g (1.5 mmol )Compound X6 : 0.55 g (2.2 mmol)DMF: 20 mlBis(dibenzylideneacetone) palladium( 0 ) : 0.84 g (1.5 mmol )l,8-Diazabicyclo[5.4.0]undec-7-ene: 0.44 g (2.9 mmol) Tricyclohexylphosphine : 0.81 g (2.9 mmol)[0105] Next, the reaction solution was heated to 150 C and stirred at this temperature (150 C) for 4 hours. Next, the reaction solution was cooled and then concentrated under reduced pressure to produce a dark-red solid. The resultant solid was purified by column chromatography (developing solvent; toluene : heptane = 1:3) and then recrystallized with chloroform/methanol to produce 247 mg of dark-red exemplified compound XX-1 (yield: 26%).
  • 45
  • [ 1232679-86-5 ]
  • [ 73183-34-3 ]
  • [ 68716-52-9 ]
  • 47
  • [ 79-01-6 ]
  • [ 68716-52-9 ]
  • [ 83671-21-0 ]
  • 48
  • [ 106-38-7 ]
  • [ 68716-52-9 ]
  • [ 27331-34-6 ]
  • 49
  • [ 1548389-35-0 ]
  • [ 68716-52-9 ]
  • [ 1548389-42-9 ]
YieldReaction ConditionsOperation in experiment
78% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70℃; for 5h; 3.67 g (10.0 mmol) of Intermediate I-7b (which was produced by substituting a hydrogen of Intermediate I-7a with deuterium), 2.54 g (10.0 mmol) of <strong>[68716-52-9]4,4,5,5,-tetramethyl-2-naphthalen-1-yl-[1,3,2]dioxaborolane</strong>, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.15 g (30.0 mmol) of K2CO3 were dissolved in 50 mL of a mixed solution of THF/H2O (2:1), which was then stirred at about 70 C. for about 5 hours. The reaction solution was cooled to room temperature, followed by extraction three times with 50 mL of water and 50 mL of diethylether. The collected organic phase was dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified using silica gel column chromatography to obtain 3.23 g of Intermediate I-8b (Yield: 78%). This compound was identified using MS/FAB. C30H14D12O: calc. 414.60. found 414.72
78% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70℃; for 5h; Intermediate I-7a in intermediates I-7b substituting hydrogen of the methyl group with deuterium of 3.67g (10.0 mmol), 4,4,5,5- tetramethyl-2-naphthalen-l-yl[l, 3,2]dioxaborolane(4,4,5,5-Tetramethyl-2-naphthalen-1-yl- [1,3,2]dioxaborolane) 2.54g (10.0mmol), Pd (PPh3) 4 0.58 g (0.5 mmol) , K2CO3 4.15 g (30.0 mmol) and THF / H2O (2/1, v / v) mixed solution was dissolved in 50 After stirred at 70 C for 5 hours. After cooling the reaction solution to room temperature and extracted three times with diethyl ether and water 50ml . The combined organic layers were dried over magnesium sulfate, and separation of the residue obtained by evaporation of the solvent in jelgwan silica chromatography to yield the intermediate I-8b 3.23g (yield: 78%). The resulting compound was confirmed by MS / FAB. C30H14D12O calculated 414.60, 414.72 measure
  • 50
  • [ 1401094-66-3 ]
  • [ 68716-52-9 ]
  • [ 1533422-51-3 ]
YieldReaction ConditionsOperation in experiment
63% With Pd(OTf)2(CH3CN)4; sodium hydrogencarbonate; N-acetyl-D-tert-leucine; silver carbonate; p-benzoquinone; In water; dimethyl sulfoxide; tert-butyl alcohol; at 100℃; for 18h;Inert atmosphere; Schlenk technique; General procedure: In a 50 ml Schlenk tube, starting material 1 (49.8 mg, 0.2 mmol), 4-methoxycarbonylphenylboronic acid pinacol ester (2) (104.8 mg, 0.4 mmol),Pd(OTf)2(MeCN)4 (11.4 mg, 0.02 mmol), Ac-D-tLeu-OH (3) (6.9 mg, 0.04 mmol),NaHCO3 (100.8 mg, 1.2 mmol), Ag2CO3 (110.3 mg, 0.4 mmol) and 1,4-benzoquinone (10.8 mg, 0.1 mmol) were combined. The flask was evacuated and backfilled with N2 three times, before a solution of dimethylsulfoxide (DMSO,6.0 mg, 0.076 mmol), water (20 mg, 1.1 mmol) and t-amyl-OH (1 ml, 0.2 M) was added. The reaction mixture was then stirred at 100 8C for 18 hours. After being allowed to cool to room temperature, the mixture was diluted with a 1:1 mixture of hexanes:ethyl acetate, and filtered through a pad of celite. The filtrate was concentrated in vacuo, and the resulting residue purified by column chromatography using an eluent of hexanes:ethyl acetate. The product, 1b, was obtained as a light-yellow liquid (62.9 mg, 82%).The above procedure to prepare 1b is generally representative for all the products shown in Tables 3 and 4. Any deviations from this protocol are specified in the footnotes of the tables.
  • 51
  • [ 73183-34-3 ]
  • [ 90-13-1 ]
  • [ 68716-52-9 ]
YieldReaction ConditionsOperation in experiment
80% With (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; dichlorobis(trimethylphosphine)nickel; In tetrahydrofuran; at 100℃; for 2h;Inert atmosphere; Sealed tube; Under an argon atmosphere,4.2 mg (0.015 mmol) of dichlorobis (trimethylphosphine) nickel,80.5 mg (0.5 mmol) of 1-chloronaphthalene,152 mg (1.0 mmol) of cesium fluoride,153 mg (0.6 mmol) of 4,4,5,5,4 ', 4', 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolanyl)180 mg (1.05 mmol) of trimethyl (2,2,2-trifluoroethoxy) silane and 0.5 mL of tetrahydrofuran were added and sealed,Followed by stirring at 100 C. for 2 hours. After cooling the reaction vessel to room temperature,1 mL of a saturated aqueous solution of ammonium chloride was added and the mixture was extracted three times with 8 mL of ethyl acetate,The organic phases obtained were combined.The solvent was distilled off under reduced pressure,The residue was purified using silica gel column chromatography (hexane: chloroform: ethyl acetate = 16: 4: 0 to 16: 4: 1)101 mg (white solid, yield 80%) of 2- (1-naphthyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was obtained
  • 52
  • [ 1610455-49-6 ]
  • [ 68716-52-9 ]
  • (1R,2R)-N-(4-cyano-2,3,5,6-tetrafluorophenyl)-1-ethyl-2-(naphthalen-1-yl)cyclobutanecarboxamide [ No CAS ]
  • 53
  • [ 18014-00-1 ]
  • [ 68716-52-9 ]
  • [ 1054613-92-1 ]
YieldReaction ConditionsOperation in experiment
86% Di<strong>[18014-00-1]methyl 2,5-dibromoterephthalate</strong> (3.0 g, 8.53 mmol), 1-naphthaleneboronic acid (3.39 g, 19.73 mmol), toluene (100 mL), potassium carbonate aqueous solution (40 mL, 2M, 80 mmol) and 3 drops of aliquat 336 were added to a 250 mL flask flushed with nitrogen. The mixture was bubbled with nitrogen for 0.5 h, then Pd(PPh3)4 (0.79 g, 0.68 mmol) was added. The mixture was stirred, heated at reflux for 48 h under nitrogen. It was then cooled, diluted with water and extracted with toluene. The organic phase was dried over anhydrous MgSO4 and evaporated to yield a white solid: 3.31 g, 86% yield. 1H NMR (400 MHz, CDCl3, d): 8.06 (s, 2H), 7.95e7.91 (m, 4H), 7.67e7.41 (m, 10H), 3.39 (d, J 4.0 Hz, 6H).
  • 54
  • [ 68716-52-9 ]
  • [ 1263048-18-5 ]
  • 55
  • [ 68716-52-9 ]
  • [ 1604784-82-8 ]
  • 56
  • [ 68716-52-9 ]
  • C52H70O2 [ No CAS ]
  • 57
  • [ 134-32-7 ]
  • [ 73183-34-3 ]
  • [ 68716-52-9 ]
YieldReaction ConditionsOperation in experiment
85% General procedure: To a solution of arylamine (0.5 mmol, 1.0 equiv) in MeOH(1.0 mL) was added HCl (0.5 mL, 1.5 mmol, 3.0 equiv) followed by H2O (0.5 ml). This mixture was stirred 2 min, and the NaNO2 solution (0.25 mL) was then added. The NaNO2 solution was prepared by dissolving 35 mg of NaNO2 in H2O (0.25 mL). This mixture was stirred 30 minat 0-5 C followed by B2pin2 (2, 381 mg, 1.5 mmol, 3.0equiv) in MeOH (1.0 mL). This mixture was stirred 60 min.H2O (10 mL) was added to the reaction mixture, then extracted with CH2Cl2 (50 mL, 3×). The combined organic layers were washed with sat. NaHCO3, dried over Na2SO4, followed by evaporation, and the crude residue was purified by flash chromatography.
78% General procedure: An arylamine (50 mmol) was dissolved in 50% hydrofluoroboric acid(17 mL) and water (20 mL). After cooling the reaction mixture to 0 C, a solution of sodium nitrite (3.4 g in 7.5 mL water) was added dropwise to the reaction system (over 5 min). The resulting mixture was stirred for 1h and the precipitate was collected by filtration. It was redissolved in the minimum amount of acetone and then diethyl ether was added to precipitate the aryl diazonium tetrafluoroborate. The product was filtered, washed with diethyl ether and dried under reduced pressure. Borylation of aryldiazonium salts; general procedure The aryldiazonium salt (0.5 mmol) and (Bpin)2 (0.75 mmol) were added to an oven-dried Schlenk tube. The tube was evacuated and backfilled with argon (three times). CH3OH (0.8 mL) was added to this Schlenk tube. The tube was sealed and the mixture was stirred at room temperature (22-25 C) for 36 h. After evaporation of the solvent, the residue was purified by column chromatography to afford the product.The arylboronates were purified by chromatography on a silica column eluting with petroleum ether (boiling range 60-90 C) or a petroleumether/ethyl acetate mixture (ca. 60:1) by volume giving Rf values for the boronates of ca. 0.2-0.3.
68% General procedure: Aryl amine (10 mmol) was dissolved in a mixture of 5 mL of distilled water and 3.4 mL of 50% hydrofluoroboric acid. After cooling the reaction mixture to 0 C using ice bath and the sodium nitrite (0.69 g in 2 mL distilled water), was added dropwise in 5 min interval of time. The resulting mixture was stirred for 1 h and the precipitate was collected by filtration and redissolved in minimum amount of acetone. Diethylether was added until precipitation of aryl diazonium tetrafluoroborate, which is filtered, washed several times with diethyl ether and dried under vacuum. Typical reaction procedure: General procedure: Diazonium tetrafluoroborate salts (0.5 mmol) and B2pin2 (1.5 mmol) were transferred into an oven-dried tube under air. Then acetone/H2O (2/1, 4 mL) were added into the tube via syringe. The sealed tube was keep at 20 C and stirred for 1-2 h. After the reaction was complete, dichloromethane was added to extract the product and the combined organic solution was dried by Na2SO4. The pure product was isolated after column chromatography on silica gel (petroleum ether/ethyl acetate).
  • 58
  • [ 69214-09-1 ]
  • [ 68716-52-9 ]
  • 5-(naphthalen-1-yl)imidazo[1,2-a]pyridine [ No CAS ]
  • 59
  • [ 68716-52-9 ]
  • imidazo[5,1,2-de]naphtho[1,8-ab]quinolizine [ No CAS ]
  • 60
  • [ 68716-52-9 ]
  • dimethyl benzo[de]indolizino[3,4,5-ab]isoquinoline-1,2-dicarboxylate [ No CAS ]
  • 62
  • [ 75264-92-5 ]
  • [ 68716-52-9 ]
  • [ 1447204-45-6 ]
  • 63
  • [ 76-09-5 ]
  • 2-B-((N,N-diisopropylamino)-1-naphth-1-yl)-borane [ No CAS ]
  • [ 68716-52-9 ]
YieldReaction ConditionsOperation in experiment
General procedure: In a reaction flask charged with CTA-NTf2 (100 mg) under argon atmosphere were added, in this following order: anhydrous toluene (4 mL), distilled iPr2NH (0.42 mL, 3 mmol), arylbromide (1 mmol),and amine-borane complex (0.3 mL, 2 mmol). The reaction mixture was then heated at 110 C for 16 h. After total consumption of either starting material, the reaction mixture was cooled at -5 C,quenched with anhydrous MeOH (2 mL), and stirred for 1 h at room temperature. All volatiles were removed under vacuum before adding pinacol (153 mg, 1.3 mmol) and Et2O (2 mL), and the mixture was stirred for 4 h at room temperature. Then the reaction mixture was diluted with Et2O (10 mL), and the organic phase was washed first with a solution of HCl (0.1 N, 210 mL), followed by an aqueous solution of CuCl2 (50 g/L, 310 mL), dried over Na2SO4, filtered, and concentrated under vacuum. The crude oil was passed through a pad of silica gel, eluting with Et2O. The resulting filtrate was concentrated under vacuum and eventually purified by flash chromatography if some impurities were present in the residue.
  • 64
  • [ 90-11-9 ]
  • [ 68716-52-9 ]
  • 65
  • [ 24424-99-5 ]
  • [ 68716-52-9 ]
  • [ 66821-79-2 ]
  • 66
  • [ 373-53-5 ]
  • [ 68716-52-9 ]
  • [ 55831-10-2 ]
  • 67
  • [ 53811-50-0 ]
  • [ 68716-52-9 ]
  • 2,3-dimethoxy-6-naphthalen-1-yl-benzaldehyde [ No CAS ]
  • 68
  • [ 1351445-39-0 ]
  • [ 73183-34-3 ]
  • [ 68716-52-9 ]
  • 69
  • [ 86-56-6 ]
  • [ 68716-52-9 ]
  • 70
  • [ 68716-52-9 ]
  • [ 36793-27-8 ]
  • 7,7,9-trimethyl-9-(naphthalen-1-ylmethyl)-1,4-dioxa-8-azaspiro[4.5]decane [ No CAS ]
  • 71
  • [ 10075-72-6 ]
  • [ 73183-34-3 ]
  • [ 68716-52-9 ]
  • 73
  • [ 10072-09-0 ]
  • [ 68716-52-9 ]
  • 3-(naphthalen-1-ylmethyl)pyridine [ No CAS ]
  • 74
  • [ 89751-95-1 ]
  • [ 68716-52-9 ]
  • [ 1078758-79-8 ]
  • 75
  • [ 104-21-2 ]
  • [ 68716-52-9 ]
  • [ 32891-88-6 ]
  • 76
  • 3-Cyanobenzyl acetate [ No CAS ]
  • [ 68716-52-9 ]
  • 3-(naphthalene-1-ylmethyl)benzonitrile [ No CAS ]
  • 77
  • [ 140-11-4 ]
  • [ 68716-52-9 ]
  • [ 611-45-0 ]
  • 78
  • [ 577-19-5 ]
  • [ 68716-52-9 ]
  • [ 5415-59-8 ]
YieldReaction ConditionsOperation in experiment
83% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 12h; Sub 4-a-1 (45.4 g, 179 mmol), 1-bromo-2-nitrobenzene (36.1 g, 179 mmol) obtained above,After adding K2CO3 (74.1 g, 536 mmol) and Pd (PPh3) 4 (12.4 g, 10.7 mmol) into a round bottom flask After adding THF (800 mL) and water (400 mL), the mixture was refluxed at 80 C. for 12 hours.When the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH2Cl2, and wiped with water.After drying and concentrating the organic layer with MgSO4, the resulting organic material was silicagel column.Separated to obtain the desired product 37.0 g (yield: 83%).
82% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate; In ethanol; water; toluene; at 80℃; for 16h; Intermediate I-1 2.54 g (10.0 mmol), 1-bromo-2-nitrobenzene 2.02 g (10.0 mmol), Pd (PPh3) 4 0.58 g (0.50 mmol),TBAB ( Tetrabutylammonium bromide ) 0.16 g ( 0.5 mmol ) and 3.18 g Na2CO3 ( 30.0 mmol ) of toluene / ethanol / H2O( 3/3/1 ) and then dissolved in a mixed solution of 60 mL , and stirred at 80C for 16 hours. The reaction solution was cooled to room temperature , waterTo 60 mL and 60 mL of diethyl ether and extracted three times . Dry the organic layer obtained therefrom by magnesium sulfate, and the solventThe residue obtained by evaporation purified by silica gel column chromatography to obtain the Intermediate I - 2 2.04 g ( yield 82%)
82% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate; In ethanol; water; toluene; at 80℃; for 16h; Intermediate I-9 2.54 g (10.0 mmol), 1 - bromo-2-nitrobenzene 2.02 g (10.0 mmol), Pd (PPh3) 4 0.58 g (0.50 mmol), tetrabutylammonium bromide (Tetrabutylammonium bromide) (hereinafter, TBAB) 0.16 g (0.5 mmol) and 3.18 g Na2CO3 (30.0 mmol) in toluene / ethanol / H2O (3/3/1) and then dissolved in a mixed solution of 60 mL, 80 from 16 sigan dongan stirring. reaction The solution was cooled to room temperature and extracted three times with 60 mL water and 60 mL of diethyl ether. Dry the organic layer obtained therefrom by magnesium sulfate, and purified the residue obtained by evaporating the solvent was subjected to silica gel column chromatography to give the intermediate I-10 2.04 g (82% yield). The resulting compound was confirmed by LC-MS.
  • 79
  • [ 68716-52-9 ]
  • C35H24NP [ No CAS ]
  • 80
  • [ 68716-52-9 ]
  • C35H24NOP [ No CAS ]
  • 81
  • [ 68716-52-9 ]
  • [ 92855-12-4 ]
  • 82
  • [ 68716-52-9 ]
  • [ 1442461-86-0 ]
YieldReaction ConditionsOperation in experiment
79% With sodium t-butanolate; In tetrahydrofuran; toluene; at 120℃; for 6h;Sealed tube; General procedure: 1-methoxy-4-iodobenzene (47 mg, 0.20 mmol) was reacted with 1,1-diboxoethane (114 mg, 0.40 mmol) and sodium tert-butoxide base (38 mg, 0.40 mmol) was placed in a 4 mL vial.Toluene / tetrahydrofuran (2.0 mL, 1: 1 mixed solution) was then added.This vial is sealed with PTFE / silicone coated cap 6 hours at 120 oC The reaction proceeded.The reaction solution was filtered through celite with dichloromethane, and the organic material was concentrated under reduced pressure. As a resultThe formation of the boronated compound 2- (4-Methoxyphenyl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane was confirmed by nuclear magnetic resonance imaging apparatus and gas chromatography apparatus. (Yield of 35 mg, 75%);
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In toluene; for 24h; General procedure: Sub 2-1-3 (4.14g, 20mmol) was dissolved in toluene, bis-pinacolato diboron (5.58g, 22mmol), Pd(dppf)Cl2 catalyst (0.44g, 0.6mmol), KOAc (5.89g, 60mmol )was added. A borate compound was synthesized by stirring for 24 hours after the addition, as, after the thus obtained compound was separated over a silicagel column and recrystallized to obtain 3.8g of Sub 2 (3). (Yield: 75%)
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 90 - 100℃; General procedure: After the bromine compound (1 equivalent) was dissolved in DMF,Bis (pinacolato) diboron (1.1 eq.), Pd (dppf) Cl2 (0.03 mmol)After addition of KOAc (3 eq) And stirred at 90 to 100 C. When the reaction was complete, DMF was removed by distillation and extracted with CH2Cl2 and water.The organic layer was dried over MgSO4 and concentrated. The resulting compound was purified by silicagel column and recrystallized to give product Sub2.
  • 84
  • C20H11ClN2 [ No CAS ]
  • [ 68716-52-9 ]
  • C30H18N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In tetrahydrofuran; water; at 80 - 90℃; To a round bottom flask Sub 1 (6) (6.3g, 20mmol) and the mixture, Sub 2 (2) (5.1g, 20mmol), Pd (PPh3) 4 (0.7g, 0.6mmol), NaOH (2.4g, 60mmol) , THF (60 mL), put the water (30mL). Then heated to reflux while 80 ~ 90C . After completion of reaction, diluted with distilled water at room temperature and extracted with methylene chloride and water. The resulting compound was concentrated by drying the organic layer with MgSO4 silicagel column and recrystallized to obtain 6.2g of 6-2. (Yield: 76%)
  • 85
  • [ 68716-52-9 ]
  • C23H14BrN [ No CAS ]
  • 86
  • [ 607-68-1 ]
  • [ 68716-52-9 ]
  • 2-chloro-4-(naphthalene-1-yl)quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 90℃; Phenylboronic acid pinacol ester (22.3 g, 109 mmol), THF (240 ml), 2, 4, 6-trichloropyrimidine (10 g, 54.5 mmol), Pd (PPh 3) 4 (3.8 g, 3.27 mmol), K 2 CO 3 (45.2 g, 327 mmol), water (120 ml) adding an 90 C stirring section. When reaction is completed CH 2 Cl 2 and a water extraction of organic layer after MgSO 4 to dry a formed after silicagel column are 9.5 g obtained for the products and recrystallization. (Yield: 65%) Phenylboronic acid pinacol ester (19.2 g, 75.4 mmol), THF (332 ml), 2,4 dichloroquinazoline (15 g, 75.4mmol), Pd (PPh3) 4 (2.6 g, 2.26 mmol), K2CO3 (31.2 g, 226 mmol) , water (166 ml) to give 9.64 g of the product using the Sub 2-25 synthesis. (Yield: 49%)
  • 87
  • C28H17BrN2 [ No CAS ]
  • [ 68716-52-9 ]
  • C38H24N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 90℃; for 4h; Intermediate product (F) 10.0 g (21.6 mmol), 4,4,5,5- tetramethyl-2-naphthalen-l-yl [l, 3,2] dioxane is to Sabo 4.1g (23.8 mmol) and tetra tetrakis (triphenylphosphine) palladium [Pd (PPh3) 4] 0.8 g (0.7 mmol) in tetrahydrofuran (THF) 100 ml solvent in dissolved, then potassium carbonate (K2CO3), 6.6 g (47.6 mmol) water 50 ml solution was added and the reaction for 4 hours at 90 dissolved in the. After confirming the completion of the reaction by thin layer chromatography (TLC) and cool. After filtering the solution and wash with water and a large amount of methanol. The resulting solid was recrystallized with chlorobenzene to obtain a compound B-1 (G) to 9.7 g (yield: 88.0%) was obtained.
Same Skeleton Products
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