Home Cart 0 Sign in  
X

[ CAS No. 10262-65-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
3d Animation Molecule Structure of 10262-65-4
Chemical Structure| 10262-65-4
Chemical Structure| 10262-65-4
Structure of 10262-65-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 10262-65-4 ]

Related Doc. of [ 10262-65-4 ]

Alternatived Products of [ 10262-65-4 ]

Product Details of [ 10262-65-4 ]

CAS No. :10262-65-4 MDL No. :MFCD03964189
Formula : C13H11BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :HHHKEQGAGUAOQI-UHFFFAOYSA-N
M.W : 279.13 Pubchem ID :193452
Synonyms :

Calculated chemistry of [ 10262-65-4 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.15
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 68.5
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.42
Log Po/w (XLOGP3) : 3.62
Log Po/w (WLOGP) : 3.43
Log Po/w (MLOGP) : 2.77
Log Po/w (SILICOS-IT) : 3.86
Consensus Log Po/w : 3.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.12
Solubility : 0.0214 mg/ml ; 0.0000766 mol/l
Class : Moderately soluble
Log S (Ali) : -3.86
Solubility : 0.0385 mg/ml ; 0.000138 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.4
Solubility : 0.0011 mg/ml ; 0.00000394 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 10262-65-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P234-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P390-P405-P406-P501 UN#:3261
Hazard Statements:H290-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 10262-65-4 ]

* 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 [ 10262-65-4 ]

[ 10262-65-4 ] Synthesis Path-Downstream   1~79

  • 2
  • [ 109-06-8 ]
  • [ 10262-65-4 ]
  • 2-(6-methoxynaphthalen-2-yl)indolizine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ethanol Erwaermen des Reaktionsprodukts mit wss.Natriumhydrogencarbonat-Loesung;
  • 3
  • [ 288-32-4 ]
  • [ 10262-65-4 ]
  • 2-Imidazol-1-yl-1-(6-methoxy-naphthalen-2-yl)-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide 1.) 0 deg C, 2 h, 2.) RT, overnight;
  • 4
  • [ 3900-45-6 ]
  • [ 10262-65-4 ]
YieldReaction ConditionsOperation in experiment
95% With copper(I) bromide In ethanol at 60℃; Inert atmosphere;
93.6% With 1-butyl-3-methylimidazolium tribromide In neat (no solvent) for 0.166667h;
77% With potassium bromate; water; potassium bromide In ethanol for 0.75h;
73% With phenyltrimethylammonium tribromide In tetrahydrofuran Inert atmosphere;
58% With phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; for 2.5h; 1.1 Phenyltrimethylammoniun tribromide (9.45 g, 25.1 mmol) was added under nitrogen in portions over approximately 2 h to a solution of 1-(6-methoxy-naphthalen-2-yl)-ethanone (5.05 g, 25.2 mmol) in 50 mL of anhydrous THF at room temperature. After the addition the reaction was stirred at room temperature for 0.5 h. and then 250 mL of cold water was added. The solid present was collected by filtration, rinsed with 50 mL of water and dried under reduced pressure to give 6.66 g of a tan solid. Recrystallization of the solid from isopropyl alcohol gave 2-bromo-1-(6-methoxy-2-naphthyl)ethanone (4.07 g, 58%) as a brown solid, mp 109-112° C. Elemental Analysis for C13H11BrO2Calc'd: C, 55.94; H, 3.97; N, 0.00. Found: C, 56.03; H, 3.94; N, 0.00. Step 2: 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole. Thiobenzamide (447 mg, 3.26 mmol) was added under nitrogen to a solution of (2-bromo-1-(6-methoxy-2-naphthyl)ethanone (906 mg, 3.25 mmol), prepared in the previous step, in 25 mL of absolute ethanol at approximately 70° C. After the addition the reaction was refluxed for 2 h. The solid was collected by filtration, rinsed with absolute ethanol and dried under reduced pressure to give 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole (909 mg, 88%) as a white solid, mp 191-193° C. Elemental Analysis for C20H15NOS Calc'd: C, 75.68; H, 4.76; N, 4.41. Found: C, 75.37; H, 4.65; N, 4.31. Step 3: 6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol. A solution of 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole (804 mg, 2.53 mmol), prepared in the previous step, in 50 mL of glacial HOAc plus 25 mL of 48% HBr was stirred under nitrogen at 120° C. for 3 h. The solvent was removed under reduced pressure and the residue partitioned between 10% methanol-methylene chloride and 5% NaHCO3. (Note: The solid that did not dissolve in either layer was collected by filtration and saved as the HCL salt of the desired product). The aqueous layer was separated and extracted three times with 10% methanol-methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol (650 mg, 85%) as a brown solid, mp 194-197° C. Elemental Analysis for C19H13NOS Calc'd: C, 75.22; H, 4.32; N, 4.62. Found: C, 74.22; H, 4.12; N, 4.43 Step 4: 2-Hydroxy-3-phenyl-propionic acid methyl ester. Hydrogen chloride was bubbled for 15 minutes into a solution of 2-hydroxy-3-phenyl-propionic acid (10.0 g, 60 mmol) in 100 mL of methanol at room temperature. The vessel was sealed and then stirred overnight at room temperature. The reaction was made basic by the addition of 5% NaHCO3 and then concentrated under reduced pressure to remove the methanol. The residue was diluted with water and extracted with ethyl acetate. The organic layer was extracted with saturated NaCl, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 2-hydroxy-3-phenyl-propionic acid methyl ester (9.7 g, 90%) as a yellow oil, MS m/z 180 [M]+. Elemental Analysis for C10H12O3 Calc'd: C, 66.65; H, 6.71; N, 0.00. Found: C, 66.52; H, 6.86; N, 0.29 Step 5: 3-Phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester. Triethylamine (931 μL, 6.68 mmol) was added under nitrogen to a solution of 2-hydroxy-3-phenyl-propionic acid methyl ester (1.00 g, 5.57 mmol), prepared in the previous step, in 20 mL of chloroform (99.9%; free of ethanol) at dry ice-acetone temperature. Trifluoromethanesulfonic anhydride (1.03 mL, 6.13 mmol) was then added dropwise over 15 minutes. The cooling bath was removed and the reaction was stirred overnight at room temperature. The reaction was extracted with 1 N HCl, 5% NaHCO3, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 1.53 g a brown oil. Purification of the oil on 100 g of silica gel (230-400 mesh) using 3:1 methylene chloride:hexane as the eluent gave 3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester (1.106 g, 64%) as clear oil. Elemental Analysis for C11H11F3O5S Calc'd: C, 42.31; H, 3.55; N, 0.00. Found: C, 42.15; H, 3.35; N, 0.14 Step 6: Methyl 3-phenyl-2-[6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy} propanoate. A mixture of 6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol (247 mg, 0.814 mmol), prepared in step 3,3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester (387 mg, 1.24 mmol), prepared in the previous step, and cesium carbonate (532 mg, 1.63 mmol) in 20 mL of acetone was stirred under nitrogen at room temperature for 17 h. The reaction was concentrated under reduced pressure to remove the acetone. The residue was partitioned between methylene chloride and water. The aqueous layer was separated and extracted three times with methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 449 mg of a brown oil. Purification of the oil on 300 g of silica gel (230-400 mesh) using 1:1 to 3:2 methylene chloride:hexane as the eluent gave methyl 3-phenyl-2-[6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}propanoate (333 mg, 88%) as a white foam, MS (ESI) m/z 466 [M+H]+. Elemental Analysis for C29H23NO3S Calc'd: C, 74.82; H, 4.98; N, 3.01. Found: C, 74.46; H, 4.96; N, 2.81. Step 7: 3-Phenyl-2-[6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}propanoic acid. A mixture of methyl 3-phenyl-2-[6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy} propanoate (260 mg, 0.559 mmol), prepared in the previous step, and 1 N NaOH (839 μL, 0.839 mmol) in 40 mL of THF plus 10 mL of water was refluxed under nitrogen for 3.5 h and then stood overnight at room temperature. By TLC starting material remained. An additional 559 μL (0.559 mmol) of 1 N NaOH was added and the mixture refluxed for 3 h. The reaction was acidified by the addition of 2 mL of 1 N HCl and then concentrated under reduced pressure to remove the THF. The gum present was dissolved in methylene chloride and the mixture concentrated under reduced pressure. The solid present was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (234 mg, 92%) as a yellow solid, mp 154-160° C. Elemental Analysis for C28H21NO3S+0.2H2O Calc'd: C, 73.89; H, 4.74; N, 3.08. Found: C, 72.55; H, 4.99; N, 2.67
58% With phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; for 2.5h; 1.1 Phenyltrimethylammoniun tribromide (9.45 g, 25.1 mmol) was added under nitrogen in portions over approximately 2 h to a solution of l-(6-methoxy-naphthalen-2-yl)-ethanone (5.05 g, 25.2 mmol) in 50 mL of anhydrous THF at room temperature. After the addition the reaction was stirred at room temperature for 0.5 h. and then 250 mL of cold water was added. The solid present was collected by filtration, rinsed with 50 mL of water and dried under reduced pressure to give 6.66g of a tan solid. Recrystallization of the solid from isopropyl alcohol gave 2-bromo-l-(6-methoxy-2-naphthyl)ethanone (4.07 g, 58%) as a brown solid, mp 109-112°C. Elemental Analysis for CnHnBrOa Calc'd: C, 55.94; H, 3.97; N, 0.00. Found: C, 56.03; H, 3.94; N, 0.00.
58% With phenyltrimethylammonium tribromide In tetrahydrofuran at 20℃; for 2.5h; 1.1 Step 1: 2-Bromo-l-(6-methoxy-2-naphthyl)ethanone.Phenyltrimethylammoniun tribromide (9.45 g, 25.1 mmol) was added under nitrogen in portions over approximately 2 h to a solution of 1-(6-methoxy-naphthalen-2-yl)-ethanone (5.05 g, 25.2 mmol) in 50 mL of anhydrous THF at room temperature. After the addition the reaction was stirred at room temperature for 0.5 h. and then 250 mL of cold water was added. The solid present was collected by filtration, rinsed with 50 mL of water and dried under reduced pressure to give 6.66 g of a tan solid. Recrystallization of the solid from isopropyl alcohol gave 2-bromo-l-(6-methoxy-2-naphthyl)ethanone (4.07 g, 58%) as a brown solid, mp 109-112°C. Elemental Analysis for Ci3HnBr02 Calc'd: C, 55.94; H, 3.97; N, 0.00. Found: C, 56.03; H, 3.94; N, 0.00.
50% With pyridinium hydrobromide perbromide In tetrahydrofuran at 20℃; for 12h; Bromoacetonaphthol methyl ether 4 To a solution of 4.40 g (22.0 mmol, 1.00 mol eq) acetonaphthol methyl ether 3 in 150 mL THF and 7.70 g (24.2 mmol, 1.10 mol eq) pyridinium tribromide ware added portionwise. The mixture was stirred 12 h at rt. Then the reaction mixture was evaporated, 100 mL of water was added and the mixture extracted by EA (3 x 80 mL). Combined organic layers were washed by 2 x 100 mL of saturated aq. solution of NaCl and dried over Na2SO4. After filtration organic solution was evaporated by RVO and HV. Obtained crude product was triturated by 2 x 50 mL of acetone. Combined organic solutions were evaporated by RVO and HV to yield 3.10 g (10.99 mmol, 50 %) of bromide 4.
With copper(ll) bromide In chloroform; ethyl acetate Heating;
89 % Chromat. With tribromure de triphenylmethylphosphonium In dichloromethane at 25℃; for 4h;
With N-Bromosuccinimide In diethyl ether at 30℃; for 5h; UV-irradiation;
With copper(ll) bromide In chloroform; ethyl acetate at 80℃; for 3.75h; Inert atmosphere;
With copper(ll) bromide In ethanol for 6h; Reflux;
With copper(ll) bromide In ethanol for 6h; Reflux;
With copper(ll) bromide In chloroform; ethyl acetate for 3h; Reflux; 22 Example 22Synthesis of Compound 20 A mixture of 2.5 g of 6’-methoxy-2’-acetonaph- thone and 5.6 g of copper (II) bromide in 100 mE of CHC13/ethyl acetate (1:1 v/v) was heated at reflux tempera- tare for 3 h. Afier the reaction mixture was cooled to roomtemperature, the precipitate was filtered oil and washed withCHC13. The crude product was recrystallized from CHC13and hexanes.
With potassium peroxymonosulfate sulfate; ammonium bromide In methanol Reflux;

Reference: [1]Su, Qiong; Zhao, Zi-Jian; Xu, Feng; Lou, Peng-Cai; Zhang, Kai; Xie, De-Xun; Shi, Lei; Cai, Qing-Yun; Peng, Zhi-Hong; An, De-Lie [European Journal of Organic Chemistry, 2013, # 8, p. 1551 - 1557]
[2]Cao, Gao; Hu, Ai-Xi; Xie, Yan-Li; Zhou, Zhen [Journal of Heterocyclic Chemistry, 2013, vol. 50, # SUPPL.1, p. E126-E130]
[3]Location in patent: experimental part Thirunarayanan; Vanangamudi; Sathiyendran; Ravi [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 4, p. 593 - 604]
[4]Location in patent: experimental part Kourounakis, Angeliki P.; Matralis, Alexios N.; Nikitakis, Anastasios [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 21, p. 7402 - 7412]
[5]Current Patent Assignee: PFIZER INC - US2006/52420, 2006, A1 Location in patent: Page/Page column 13-14
[6]Current Patent Assignee: PFIZER INC - WO2006/23864, 2006, A1 Location in patent: Page/Page column 29
[7]Current Patent Assignee: PFIZER INC - WO2006/23865, 2006, A1 Location in patent: Page/Page column 32
[8]Murár, Miroslav; Dobiaš, Juraj; Šramel, Peter; Addová, Gabriela; Hanquet, Gilles; Boháč, Andrej [European Journal of Medicinal Chemistry, 2017, vol. 126, p. 754 - 761]
[9]Walker; Wallach; Hirschfeld [Journal of Medicinal Chemistry, 1981, vol. 24, # 1, p. 67 - 74]
[10]Cristau, Henri-Jean; Torreilles, Eliane; Morand, Philippe; Christol, Henri [Phosphorus and Sulfur and the Related Elements, 1985, vol. 25, p. 357 - 368]
[11]Arbuj, Sudhir S.; Waghmode, Suresh B.; Ramaswamy [Tetrahedron Letters, 2007, vol. 48, # 8, p. 1411 - 1415]
[12]Park, Hee Jung; Lim, Chang Su; Kim, Eun Sun; Han, Ji Hee; Lee, Tae Hee; Chun, Hoon Jai; Cho, Bong Rae [Angewandte Chemie - International Edition, 2012, vol. 51, # 11, p. 2673 - 2676]
[13]Location in patent: scheme or table Shi, Lei; Hu, Aixi; Xu, Jiangping; Jiang, Yiping [Chinese Journal of Chemistry, 2012, vol. 30, # 6, p. 1339 - 1344]
[14]Dou, Jie; Shi, Lei; Hu, Aixi; Dong, Minyu; Xu, Jiangping; Liu, Ailin; Jiang, Yiping [Archiv der Pharmazie, 2014, vol. 347, # 2, p. 89 - 95]
[15]Current Patent Assignee: THERMO FISHER SCIENTIFIC INC - US2016/355682, 2016, A1 Location in patent: Paragraph 0239
[16]Bangalore, Pavan K.; Vagolu, Siva K.; Bollikanda, Rakesh K.; Veeragoni, Dileep K.; Choudante, Pallavi C.; Misra, Sunil; Sriram, Dharmarajan; Sridhar, Balasubramanian; Kantevari, Srinivas [Journal of Natural Products, 2020, vol. 83, # 1, p. 26 - 35]
  • 5
  • [ 3900-45-6 ]
  • [ 10262-65-4 ]
  • [ 52997-56-5 ]
YieldReaction ConditionsOperation in experiment
1: 50 % Chromat. 2: 30 % Chromat. With 2-carboxyethyl triphenyl phosphonium tribromide In tetrahydrofuran at 25℃; for 6h;
  • 6
  • 2-(6-Methoxy-naphthalen-2-yl)-2-methyl-[1,3]dioxolane [ No CAS ]
  • [ 10262-65-4 ]
  • 2-Bromomethyl-2-(6-methoxy-naphthalen-2-yl)-[1,3]dioxolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 20 % Chromat. 2: 75 % Chromat. With triphenylmethylphosphonium tribromide In tetrahydrofuran at 25℃; for 2h;
  • 7
  • [ 10262-65-4 ]
  • [ 959-28-4 ]
  • [ 134937-97-6 ]
YieldReaction ConditionsOperation in experiment
76.5% With potassium carbonate In N,N-dimethyl-formamide
  • 8
  • [ 64-17-5 ]
  • [ 10262-65-4 ]
  • 2-Hydroxy-1-(6-methoxy-naphthalen-2-yl)-ethanone [ No CAS ]
  • 2-Ethoxy-1-(6-methoxy-naphthalen-2-yl)-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With water; silver perchlorate at 40℃; other temperatures;
  • 9
  • [ 10262-65-4 ]
  • [ 52997-56-5 ]
YieldReaction ConditionsOperation in experiment
With N,N,N-trimethylanilinium bromide
  • 10
  • [ 10262-65-4 ]
  • fusidin [ No CAS ]
  • 2-[(3R,4S,5S,8S,10S,11R,13R,14S,16S)-16-Acetoxy-3,11-dihydroxy-4,8,10,14-tetramethyl-hexadecahydro-cyclopenta[a]phenanthren-(17Z)-ylidene]-6-methyl-hept-5-enoic acid 2-(6-methoxy-naphthalen-2-yl)-2-oxo-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In acetonitrile at 50℃; for 0.5h;
  • 11
  • [ 57944-10-2 ]
  • [ 10262-65-4 ]
  • C40H31NO8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 0 - 20℃; for 24h;
YieldReaction ConditionsOperation in experiment
der Rk. mit H2O/Ethanol (Tab. 1);
YieldReaction ConditionsOperation in experiment
2-Acetyl-6-methoxy-naphthalin, Brom;
2-Diazoacetyl-6-methoxy-naphthalin, wss. HBr, Ae.;
2-Acetyl-6-methoxy-naphthalin, Trimethylphenylammoniumtribromid, THF;
2-Acetyl-6-methoxy-naphthalin, Tetramethylammoniumtribromid in Bzl., Benzoylperoxid;

  • 14
  • [ 3900-45-6 ]
  • [ 10262-65-4 ]
YieldReaction ConditionsOperation in experiment
With tetrahydrofuran
  • 15
  • [ 10262-65-4 ]
  • [ 242145-53-5 ]
  • 3-(1-p-chlorophenyl-5-methyl-1,2,3-triazol-4-yl)-4-(2-bromo-6'-methoxy-2'-acetonaphthideneamino)-5-mercapto-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In ethanol for 8h; Heating;
  • 16
  • [ 10262-65-4 ]
  • 4-amino-5-mercapto-3-(2-phenylquinolin-4-yl)-1,2,4-triazole [ No CAS ]
  • 3-(2-phenylquinolin-4-yl)-4-(2-bromo-6'-methoxy-2'-acetonaphthideneamino)-5-mercapto-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% In ethanol for 8h; Heating;
  • 17
  • [ 10262-65-4 ]
  • [ 39573-60-9 ]
  • 3-(5-methylisoxazol-3-yl)-4-(2-bromo-6'-methoxy-2'-acetonaphthideneamino)-5-mercapto-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With potassium carbonate In ethanol Heating;
  • 18
  • [ 10262-65-4 ]
  • [ 2161-85-5 ]
  • 2,6-di(6-methoxy-2-naphthoyl)-3,5-dimethyl-benzo[1,2-b;5,4-b']difuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
97.9% With potassium carbonate for 0.0416667h; Irradiation; microwave irradiation;
  • 19
  • [ 10262-65-4 ]
  • [ 2999-20-4 ]
  • [3,5-diethyl-6-(6-methoxy-naphthalene-2-carbonyl)-benzo[1,2-<i>b</i>;5,4-<i>b</i>']difuran-2-yl]-(6-methoxy-naphthalen-2-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
96.5% With potassium carbonate for 0.05h; Irradiation; microwave irradiation;
  • 20
  • [ 10262-65-4 ]
  • [ 3088-15-1 ]
  • [6-(6-methoxy-naphthalene-2-carbonyl)-3,5-diphenyl-benzo[1,2-<i>b</i>;5,4-<i>b</i>']difuran-2-yl]-(6-methoxy-naphthalen-2-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
96.2% With potassium carbonate for 0.05h; Irradiation; microwave irradiation;
  • 21
  • [ 10262-65-4 ]
  • [ 2227-79-4 ]
  • [ 878796-33-9 ]
YieldReaction ConditionsOperation in experiment
88% In ethanol at 70℃; for 2h; Heating / reflux; 1.2 Phenyltrimethylammoniun tribromide (9.45 g, 25.1 mmol) was added under nitrogen in portions over approximately 2 h to a solution of 1-(6-methoxy-naphthalen-2-yl)-ethanone (5.05 g, 25.2 mmol) in 50 mL of anhydrous THF at room temperature. After the addition the reaction was stirred at room temperature for 0.5 h. and then 250 mL of cold water was added. The solid present was collected by filtration, rinsed with 50 mL of water and dried under reduced pressure to give 6.66 g of a tan solid. Recrystallization of the solid from isopropyl alcohol gave 2-bromo-1-(6-methoxy-2-naphthyl)ethanone (4.07 g, 58%) as a brown solid, mp 109-112° C. Elemental Analysis for C13H11BrO2Calc'd: C, 55.94; H, 3.97; N, 0.00. Found: C, 56.03; H, 3.94; N, 0.00. Step 2: 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole. Thiobenzamide (447 mg, 3.26 mmol) was added under nitrogen to a solution of (2-bromo-1-(6-methoxy-2-naphthyl)ethanone (906 mg, 3.25 mmol), prepared in the previous step, in 25 mL of absolute ethanol at approximately 70° C. After the addition the reaction was refluxed for 2 h. The solid was collected by filtration, rinsed with absolute ethanol and dried under reduced pressure to give 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole (909 mg, 88%) as a white solid, mp 191-193° C. Elemental Analysis for C20H15NOS Calc'd: C, 75.68; H, 4.76; N, 4.41. Found: C, 75.37; H, 4.65; N, 4.31. Step 3: 6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol. A solution of 4-(6-methoxy-2-naphthyl)-2-phenyl-1,3-thiazole (804 mg, 2.53 mmol), prepared in the previous step, in 50 mL of glacial HOAc plus 25 mL of 48% HBr was stirred under nitrogen at 120° C. for 3 h. The solvent was removed under reduced pressure and the residue partitioned between 10% methanol-methylene chloride and 5% NaHCO3. (Note: The solid that did not dissolve in either layer was collected by filtration and saved as the HCL salt of the desired product). The aqueous layer was separated and extracted three times with 10% methanol-methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol (650 mg, 85%) as a brown solid, mp 194-197° C. Elemental Analysis for C19H13NOS Calc'd: C, 75.22; H, 4.32; N, 4.62. Found: C, 74.22; H, 4.12; N, 4.43 Step 4: 2-Hydroxy-3-phenyl-propionic acid methyl ester. Hydrogen chloride was bubbled for 15 minutes into a solution of 2-hydroxy-3-phenyl-propionic acid (10.0 g, 60 mmol) in 100 mL of methanol at room temperature. The vessel was sealed and then stirred overnight at room temperature. The reaction was made basic by the addition of 5% NaHCO3 and then concentrated under reduced pressure to remove the methanol. The residue was diluted with water and extracted with ethyl acetate. The organic layer was extracted with saturated NaCl, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 2-hydroxy-3-phenyl-propionic acid methyl ester (9.7 g, 90%) as a yellow oil, MS m/z 180 [M]+. Elemental Analysis for C10H12O3 Calc'd: C, 66.65; H, 6.71; N, 0.00. Found: C, 66.52; H, 6.86; N, 0.29 Step 5: 3-Phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester. Triethylamine (931 μL, 6.68 mmol) was added under nitrogen to a solution of 2-hydroxy-3-phenyl-propionic acid methyl ester (1.00 g, 5.57 mmol), prepared in the previous step, in 20 mL of chloroform (99.9%; free of ethanol) at dry ice-acetone temperature. Trifluoromethanesulfonic anhydride (1.03 mL, 6.13 mmol) was then added dropwise over 15 minutes. The cooling bath was removed and the reaction was stirred overnight at room temperature. The reaction was extracted with 1 N HCl, 5% NaHCO3, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 1.53 g a brown oil. Purification of the oil on 100 g of silica gel (230-400 mesh) using 3:1 methylene chloride:hexane as the eluent gave 3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester (1.106 g, 64%) as clear oil. Elemental Analysis for C11H11F3O5S Calc'd: C, 42.31; H, 3.55; N, 0.00. Found: C, 42.15; H, 3.35; N, 0.14 Step 6: Methyl 3-phenyl-2-[6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy} propanoate. A mixture of 6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthol (247 mg, 0.814 mmol), prepared in step 3,3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester (387 mg, 1.24 mmol), prepared in the previous step, and cesium carbonate (532 mg, 1.63 mmol) in 20 mL of acetone was stirred under nitrogen at room temperature for 17 h. The reaction was concentrated under reduced pressure to remove the acetone. The residue was partitioned between methylene chloride and water. The aqueous layer was separated and extracted three times with methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 449 mg of a brown oil. Purification of the oil on 300 g of silica gel (230-400 mesh) using 1:1 to 3:2 methylene chloride:hexane as the eluent gave methyl 3-phenyl-2-[6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}propanoate (333 mg, 88%) as a white foam, MS (ESI) m/z 466 [M+H]+. Elemental Analysis for C29H23NO3S Calc'd: C, 74.82; H, 4.98; N, 3.01. Found: C, 74.46; H, 4.96; N, 2.81. Step 7: 3-Phenyl-2-[6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}propanoic acid. A mixture of methyl 3-phenyl-2-[6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy} propanoate (260 mg, 0.559 mmol), prepared in the previous step, and 1 N NaOH (839 μL, 0.839 mmol) in 40 mL of THF plus 10 mL of water was refluxed under nitrogen for 3.5 h and then stood overnight at room temperature. By TLC starting material remained. An additional 559 μL (0.559 mmol) of 1 N NaOH was added and the mixture refluxed for 3 h. The reaction was acidified by the addition of 2 mL of 1 N HCl and then concentrated under reduced pressure to remove the THF. The gum present was dissolved in methylene chloride and the mixture concentrated under reduced pressure. The solid present was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (234 mg, 92%) as a yellow solid, mp 154-160° C. Elemental Analysis for C28H21NO3S+0.2H2O Calc'd: C, 73.89; H, 4.74; N, 3.08. Found: C, 72.55; H, 4.99; N, 2.67
  • 22
  • [ 10262-65-4 ]
  • [ 17518-49-9 ]
  • [ 878796-46-4 ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 2-bromo-1-(6-methoxy-2-naphthyl)ethanone; 2-(2,6-dichlorophenyl)ethanethioamide In ethanol for 3h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In methanol; dichloromethane; water 6.1 A suspension of (2-bromo-1-(6-methoxy-2-naphthyl)ethanone (500 mg, 1.79 mmol), prepared in step 1 of Example 1, in 25 mL of absolute ethanol was heated under nitrogen to reflux temperature. At this point all of the solid had dissolved. At reflux temperature 2-(2,6-dichlorophenyl)ethanethioamide (395 mg, 1.79 mmol) was added and the reaction refluxed for 3 h. After cooling to room temperature the solid was collected by filtration, rinsed with absolute ethanol and dried under reduced pressure to give 575 mg of an off-white solid. The solid was dissolved in 20% methanol-methylene chloride. An excess of 5% NaHCO3 was added to convert the amine salt to the free base. The aqueous layer was separated an extracted three times with 20% methanol-methylene chloride. The combined organic extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 2-(2,6-dichlorobenzyl)-4-(6-methoxy-2naphthyl)-1,3-thiazole (432 mg, 60%) as a light tan solid, mp 136-138° C. Elemental Analysis for C21H15Cl2NOS Calc'd: C, 62.29; H, 3.76; N, 3.45. Found: C, 62.28; H, 3.67; N, 3.35. Step 2: 6-[2-(2,6-Dichlorobenzyl)-1,3-thiazol-4-yl]-2-naphthol. A solution of 2-(2,6-dichlorobenzyl)-4-(6-methoxy-2-naphthyl)-1,3-thiazole (390 mg, 0.975 mmol), prepared in the previous step, in 50 mL of glacial HOAc plus 25 mL of 48% HBr was stirred under nitrogen at 120° C. for 3.5 h and then stood overnight at room temperature. The reaction was concentrated under reduced pressure. The residue was dissolved in 20% methanol-methylene chloride and neutralized with the addition of an excess of 5% NaHCO3. The aqueous layer was separated and extracted three times with 20% methanol-methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 6-[2-(2,6-dichlorobenzyl)-1,3-thiazol-4-yl]-2-naphthol (303 mg, 80%) as a brown solid, mp 191-193° C. Elemental Analysis for C20H13Cl2NOS Calc'd: C, 62.19; H, 3.39; N, 3.63. Found: C, 61.31; H, 3.30; N, 3.42. Step 3: Methyl ({6-[2-(2,6-dichlorobenzyl)-1,3-thiazol-4-yl]-2-naphthyl}oxy)acetate. A mixture of 6-[2-(2,6-dichlorobenzyl)-1,3-thiazol-4-yl]-2-naphthol (269 mg, 0.696 mmol), prepared in the previous step, methyl bromoacetate (79 μL, 0.835 mmol) and cesium carbonate (341 mg, 1.05 mmol) in 25 mL of acetone was stirred under nitrogen at room temperature for 4 h. The reaction was concentrated under reduced pressure to remove the acetone. The residue was partitioned between methylene chloride and water. The aqueous layer was separated and extracted three times with methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give 298 mg of a tan solid. The solid was triturated multiple times with hexane and then dried under reduced pressure to give methyl ({6-[2-(2,6-dichlorobenzyl)-1,3-thiazol-4-yl]-2-naphthyl}oxy)acetate (298 mg, 93%) as a tan solid, mp 174-177° C. Elemental Analysis for C23H17Cl2NO3S Calc'd: C, 60.27; H, 3.74; N, 3.06. Found: C, 59.03; H, 3.70; N, 2.88. Step 4: ({6-[2-(2,6-Dichlorobenzyl)-1,3-thiazol-4-yl]-2-naphthyl}oxy)acetic acid. A mixture of methyl ({6-[2-(2,6-dichlorobenzyl)-1,3-thiazol-4-yl]-2-naphthyl}oxy)acetate (205 mg, 0.447 mmol), prepared in the previous step, and 1 N NaOH (671 μL, 0.671 mmol) in 20 mL of THF plus 20 mL of methanol plus 10 mL of water was refluxed under nitrogen for 2.5 h. The reaction was filtered, acidified by the addition of 3 mL of 1 N HCl and then concentrated under reduced pressure to remove the THF and methanol. The solid present was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (150 mg, 74%) as an off-white solid, mp 205-207° C. Elemental Analysis for C22H15Cl2NO3S+0.30H2O Calc'd: C, 58.75; H, 3.50; N, 3.11. Found: C, 59.09; H, 3.58; N, 2.92.
  • 23
  • [ 10262-65-4 ]
  • [ 99-76-3 ]
  • [ 1195951-03-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; 2.1 Potassium carbonate (265 mg, 1.92 mmol, 3 eq) was added to a solution of methyl 4-hydroxy-benzoate (170 mg, 0.64 mmol, 1 eq)) and 2-bromo-1 -(6- methoxynaphthalen-2-yl)ethanone (97 mg, .64 mmol, 1. eq) in DMF (2 ml_) at room temperature. After stirring the reaction mixture for 1.5h, one half of the reaction mixture was partitioned between dilute aqueous HCI and 2:1 EtOAc:hexanes. The aqueous layer was discarded and the organic layer was washed twice with brine. The organic layer was dried over anhydrous MgSO4, filtered and evaporated to afford the desired product (128 mg) as a crude yellow solid which was used in the next step without further purification.
  • 24
  • [ 871250-54-3 ]
  • [ 10262-65-4 ]
  • [ 1195950-95-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide for 90h; 1.2 Potassium carbonate (622 mg, 4.50 mmol, 1.5 eq) was added to a solution of the benzamide prepared in Step 1 (796 mg, 3.00 mmol, 1 eq)) and 2-bromo-1-(6- methoxynaphthalen-2-yl)ethanone (Organic Syntheses, Coll. Vol. 6, p. 175 (1988); Organic Syntheses, Vol. 53, p.111 (1973), 837 mg, 3.00 mmol, 1 eq) in DMF (10 ml_). After stirring the reaction mixture for 9Oh, the reaction was partitioned between dilute brine and 2:1 EtOAc:hexanes. The aqueous layer was discarded and the organic layer was washed with aqueous 0.5M NaOH and brine twice. The organic layer was dried over MgSO4, filtered and evaporated to afford a crude yellow solid which was purified via silica gel chromatography (gradient elution: 0% to 100% EtOAc in hexanes) to afford the desired product as an off- white solid (930 mg).
  • 25
  • [ 10262-65-4 ]
  • [ 94-02-0 ]
  • [ 877379-61-8 ]
YieldReaction ConditionsOperation in experiment
85.2% Stage #1: ethyl 3-oxo-3-phenylpropionate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1.5h; Stage #2: 2-bromo-1-(6-methoxy-2-naphthyl)ethanone In N,N-dimethyl-formamide for 2h; 1.2 NaH(60%, 1.58 g, 35.8 mmol) was added under nitrogen in 4 equal portions over a 30-minute period to a stirring solution of ethyl benzoylacetate (6.89 g, 35.8 mmol) in 100 mL of anhydrous DMF. After complete addition of the NaH, the mixture was allowed to stir under nitrogen at ambient temperature for 1 hour. After 1 hour, a solution of 2-bromo-l-(6-methoxy-2-naphthyl)ethanone (10.0 g, 35.8 mmol), prepared in the previous step, in 100 mL of anhydrous DMF was addeddrojWtoe via' No.fJrSSMreLeqffiaI'ffli:ig"
  • 26
  • [ 24424-99-5 ]
  • [ 10262-65-4 ]
  • [ 877378-76-2 ]
YieldReaction ConditionsOperation in experiment
32% Stage #1: di-<i>tert</i>-butyl dicarbonate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: 2-bromo-1-(6-methoxy-2-naphthyl)ethanone In N,N-dimethyl-formamide at 20℃; for 4h; Stage #3: With hydrogenchloride; water In N,N-dimethyl-formamide 1.2 Sodium hydride (1.88 g of a 60% dispersion in mineral oil, 47.0 mmol) was added under nitrogen to a solution of di-tert-butyl dicarbonate (7.79 g, 35.9 mmol) in 100 mL of anhydrous DMF at room temperature. After the addition the reaction was stirred at room temperature for 2 h. 2-Bromo-l-(6-methoxy-2-naphthyl)ethanone (10.01 g, 35.9 mmol), prepared in the previous step, was then added all at once and the stirring continued at room temperature for 4 h. The reaction was quenched by the addition of 1 N HC1 and then partitioned between 1 N HC1 and ethyl acetate. The layers were separated. The organic layer was extracted five times with water, dried (MgSC>4), filtered and the solvent removed under reduced pressure to give 15.24 g of a yellow foam. Purification of the yellow foam on 1 Kg of silica gel (230-400 mesh) using 4:1 hexane:ethyl acetate as the eluent gave 11.55 g of an off-white solid. Recrystallization of the solid from isopropyl alcohol gave di(tert-butyl) 2-(6-methoxy-2-naphthyl)-2-oxoethylimidodicarbonate (4.73 g, 32%) as a white solid, mp 126-128°C. Elemental Analysis for C23H29NO6 Calc'd: C, 66.49; H, 7.04; N, 3.37. Found: C, 66.46; H, 7.09; N, 3.35.
  • 27
  • [ 109-83-1 ]
  • [ 10262-65-4 ]
  • [ 836595-06-3 ]
YieldReaction ConditionsOperation in experiment
In acetone at 20℃;
  • 28
  • [ 10262-65-4 ]
  • [ 20431-81-6 ]
  • 2-(6-methoxynaphthalen-2-yl)-4-methyl-octahydro-1,4-benzoxazin-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetone at 20℃;
  • 29
  • [ 10262-65-4 ]
  • [ 3433-37-2 ]
  • [ 1256697-79-6 ]
YieldReaction ConditionsOperation in experiment
In acetone at 20℃;
  • 30
  • [ 532-32-1 ]
  • [ 10262-65-4 ]
  • [ 62244-94-4 ]
YieldReaction ConditionsOperation in experiment
71% With water In ethanol for 4h; Reflux;
  • 31
  • [ 10262-65-4 ]
  • [ 151721-32-3 ]
  • C26H21NO5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetonitrile at 20℃; for 8h; Inert atmosphere;
  • 32
  • [ 10262-65-4 ]
  • [ 792879-88-0 ]
YieldReaction ConditionsOperation in experiment
0.33 g Stage #1: 2-bromo-1-(6-methoxy-2-naphthyl)ethanone With hexamethylenetetramine In chloroform at 20℃; Stage #2: With hydrogenchloride; water In ethanol at 45℃; for 4h; Stage #3: With sodium hydroxide In ethanol; water at 20℃;
  • 33
  • [ 10262-65-4 ]
  • [ 910776-50-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-methyl-pyrrolidin-2-one / 2 h / 60 °C 2: formic acid / 18 h / 180 °C
  • 34
  • [ 10262-65-4 ]
  • [ 1243257-38-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1-methyl-pyrrolidin-2-one / 2 h / 60 °C 2: formic acid / 18 h / 180 °C 3: triethylamine / tetrahydrofuran / 6 h / 20 °C
  • 35
  • [ 10262-65-4 ]
  • [ 111-42-2 ]
  • C17H22BrNO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1-methyl-pyrrolidin-2-one at 60℃; for 2h;
  • 36
  • [ 10262-65-4 ]
  • C18H23O5PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: methanol / 0.25 h / 20 °C / Inert atmosphere 2.1: lithium hexamethyldisilazane / tetrahydrofuran; ethylbenzene / 0.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 - 20 °C / Inert atmosphere
  • 37
  • [ 10262-65-4 ]
  • [ 1391948-81-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 0.08 h / Inert atmosphere 1.2: Inert atmosphere 2.1: lithium hexamethyldisilazane / tetrahydrofuran; ethylbenzene / 0.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 - 20 °C / Inert atmosphere 3.1: lithium hexamethyldisilazane / tetrahydrofuran; ethylbenzene / 1 h / -78 °C / Inert atmosphere
  • 38
  • [ 10262-65-4 ]
  • C19H25O5PS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium methylate / methanol / 0.08 h / Inert atmosphere 1.2: Inert atmosphere 2.1: lithium hexamethyldisilazane / tetrahydrofuran; ethylbenzene / 0.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 - 20 °C / Inert atmosphere
  • 39
  • [ 10262-65-4 ]
  • C34H40O10P2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodiumsulfide nonahydrate / water; acetone / 1 h / 20 °C / Cooling with ice; Inert atmosphere 2.1: lithium hexamethyldisilazane / tetrahydrofuran; ethylbenzene / 0.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 - 20 °C / Inert atmosphere
  • 40
  • [ 10262-65-4 ]
  • [ 1391976-33-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodiumsulfide nonahydrate / water; acetone / 1 h / 20 °C / Cooling with ice; Inert atmosphere 2.1: lithium hexamethyldisilazane / tetrahydrofuran; ethylbenzene / 0.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 - 20 °C / Inert atmosphere 3.1: lithium hexamethyldisilazane / tetrahydrofuran; ethylbenzene / 1 h / -78 °C / Inert atmosphere
  • 41
  • [ 10262-65-4 ]
  • [ 1391948-70-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: methanol / 0.25 h / 20 °C / Inert atmosphere 2.1: lithium hexamethyldisilazane / tetrahydrofuran; ethylbenzene / 0.5 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 - 20 °C / Inert atmosphere 3.1: lithium hexamethyldisilazane / tetrahydrofuran; ethylbenzene / 1 h / -78 °C / Inert atmosphere
  • 42
  • [ 10262-65-4 ]
  • [ 1391976-39-8 ]
YieldReaction ConditionsOperation in experiment
90% With sodiumsulfide nonahydrate In water; acetone at 20℃; for 1h; Cooling with ice; Inert atmosphere;
  • 43
  • [ 10262-65-4 ]
  • [ 5188-07-8 ]
  • [ 1391948-69-8 ]
YieldReaction ConditionsOperation in experiment
77% In methanol at 20℃; for 0.25h; Inert atmosphere;
  • 44
  • [ 10262-65-4 ]
  • [ 75-08-1 ]
  • [ 1391948-80-3 ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: ethanethiol With sodium methylate In methanol for 0.0833333h; Inert atmosphere; Stage #2: 2-bromo-1-(6-methoxy-2-naphthyl)ethanone In methanol Inert atmosphere;
  • 45
  • [ 10262-65-4 ]
  • [ 141-43-5 ]
  • [ 1155458-59-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-bromo-1-(6-methoxy-2-naphthyl)ethanone; ethanolamine In 1-methyl-pyrrolidin-2-one at 20 - 60℃; for 1.5h; Stage #2: With formic acid In 1-methyl-pyrrolidin-2-one at 20℃; Reflux;
  • 46
  • [ 10262-65-4 ]
  • [ 111-42-2 ]
  • [ 910776-50-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-bromo-1-(6-methoxy-2-naphthyl)ethanone; 2,2'-iminobis[ethanol] In 1-methyl-pyrrolidin-2-one at 60℃; for 2h; Stage #2: With formic acid In 1-methyl-pyrrolidin-2-one at 180℃; for 18h;
  • 47
  • [ 109-06-8 ]
  • [ 10262-65-4 ]
  • [ 1603829-39-5 ]
YieldReaction ConditionsOperation in experiment
In acetone for 4h; Reflux; General procedure for the preparation of 4a-f General procedure: A solution of 2-picoline (1) (20mmol; 1.86g; 2mL) and α-bromo-ketone (2) (20mmol) in acetone (100mL) was heated at reflux for 4h. The quaternary salt was isolated via filtration and re-dissolved in hot (60-80°C) water (100mL). K2CO3 (2.76g; 20mmol) was added and the mixture heated at 80°C for 8h. After filtration and drying in vacuum, the products of type 4 were obtained.
  • 48
  • [ 10262-65-4 ]
  • 2-(6-methoxynaphthalen-2-yl)indolizine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetone / 4 h / Reflux 2: potassium carbonate / water / 80 °C
  • 49
  • [ 10262-65-4 ]
  • [ 1603829-38-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: acetone / 4 h / Reflux 2.1: potassium carbonate / water / 80 °C 3.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 5 h / -78 - -20 °C / Inert atmosphere 3.2: 0.25 h / -40 °C / Inert atmosphere 3.3: 60 °C / Inert atmosphere
  • 50
  • [ 10262-65-4 ]
  • 2-(2-furanyl)-1-[2-(6-methoxy-2-naphthyl)ethynyl]-1H-benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 12 h / Reflux 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 2.2: 0.5 h / 0 - 20 °C / Inert atmosphere 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
  • 51
  • [ 10262-65-4 ]
  • C28H27N2O6P [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 12 h / Reflux 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 2.2: 0.5 h / 0 - 20 °C / Inert atmosphere
  • 52
  • [ 10262-65-4 ]
  • C21H30O8P2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: toluene / 12 h / Reflux 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 2.2: 0.5 h / -20 - 20 °C / Inert atmosphere
  • 53
  • [ 10262-65-4 ]
  • P-(2-(6-methoxy-2-naphthalenyl)ethynyl)-diethyl phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: toluene / 12 h / Reflux 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 2.2: 0.5 h / -20 - 20 °C / Inert atmosphere 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: toluene / 24 h / 20 °C / Sealed tube 2: triethylamine; 2-chloro-1-methyl-pyridinium iodide / dichloromethane / 3 h / 20 °C / Sealed tube
  • 54
  • [ 10262-65-4 ]
  • [ 762-04-9 ]
  • C17H21O5P [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene for 12h; Reflux;
  • 55
  • [ 3878-19-1 ]
  • [ 10262-65-4 ]
  • C24H18N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetone for 12h; Reflux;
  • 56
  • [ 5533-73-3 ]
  • [ 10262-65-4 ]
  • 1-(6-methoxy-2-naphthyl)-2-((4,5-diphenyl)triazol-2-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With potassium carbonate In acetone at 60℃; for 12h; General procedure for the synthesis of 1 General procedure: A round bottom flask (50 mL) equipped with a stirring bar was loaded with substrate 4,5-diaryltriazole (1.7 mmol), 2-bromo-1-aryl ethanone (1 mmol) and potassium carbonate (3 mmol) in 10 mL acetone. Then the mixture was kept stirred at 60 °C for 12 h. The product was purified by column chromatography using silica gel (200-300 mesh) as the stationary phase and a mixture of petroleum and dichloromethane as eluent to give pure product 1.
  • 57
  • [ 5533-73-3 ]
  • [ 10262-65-4 ]
  • 2-(6-methoxy-2-naphthylethynyl)-4,5-diphenyl-1,2,3-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetone / 12 h / 60 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / Inert atmosphere 2.2: 1 h / Inert atmosphere 2.3: 1 h / Inert atmosphere
  • 58
  • [ 10262-65-4 ]
  • [ 1001422-37-2 ]
YieldReaction ConditionsOperation in experiment
98% With sodium azide In acetone at 20℃; for 24h; Azidoacetonaphthol methyl ether 5 Sodium azide 470 mg (7.23 mmol, 1.00 mol eq) was added to a solution of 2.00 g (7.20 mmol, 1.00 mol eq) of bromoacetonaphthol methyl ether 4 in 50 mL acetone and the mixture was stirred 24 h. Then the volatile parts were evaporated by RVO, added 100 mL of brine and the mixture extracted by EA (3 x 50 mL). Combined organic layers were dried over Na2SO4 and after filtration evaporated by RVO and HV to yield 1.70 g (7.03 mmol, 98 %) of azide 5 as yellow crystals.
With sodium azide In water; acetone at 0 - 20℃;
  • 59
  • [ 10262-65-4 ]
  • N-(5-(ethylsulfonyl)-2-methoxyphenyl)-5-(6-methoxynaphthalen-2-yl)oxazol-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium azide / acetone / 24 h / 20 °C 2: triphenylphosphine / 1,4-dioxane / 0.5 h / 90 °C / Reflux
  • 60
  • [ 100-97-0 ]
  • [ 10262-65-4 ]
  • C19H23N4O2(1+)*Br(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
1g In chloroform at 0 - 20℃; 23 Example 23Synthesis of Compound 21 To 0.7 g of compound 20 in 50 mE of CHC13 at 0° C., 0.44 g of metheamine was added slowly at room temperature and stirred overnight. At the end of the period 100 mE of hexane was added to the reaction mixture and the precipitate was collected to give the product Compound 21 (1.0 g).
  • 61
  • [ 10262-65-4 ]
  • [ 153846-59-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: chloroform / 0 - 20 °C 2: hydrogenchloride / ethanol; water / 4 h / 0 - 40 °C
  • 62
  • [ 10262-65-4 ]
  • C23H16N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: chloroform / 0 - 20 °C 2: hydrogenchloride / ethanol; water / 4 h / 0 - 40 °C 3: trichlorophosphate / 10 h / Reflux
  • 63
  • [ 10262-65-4 ]
  • [ 88284-48-4 ]
  • [ 33513-42-7 ]
  • benzofuran-2-yl(6-methoxynaphthalen-2-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With potassium fluoride; 18-crown-6 ether; potassium carbonate at 60℃; for 6h;
  • 64
  • [ 10262-65-4 ]
  • [ 33513-42-7 ]
  • 2-(trimethylsilyl)naphthalen-3-yl trifluoromethanesulfonate [ No CAS ]
  • (6-methoxynaphthalen-2-yl)(naphtho[2,3-b]furan-2-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With potassium fluoride; 18-crown-6 ether; potassium carbonate at 60℃; for 6h;
  • 65
  • [ 10262-65-4 ]
  • [ 1195951-04-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: 1.42 h / 170 - 175 °C / microwave
  • 66
  • [ 10262-65-4 ]
  • [ 1195951-08-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: 1.42 h / 170 - 175 °C / microwave 3: hydrogenchloride; hydrazine hydrate / 1,4-dioxane; methanol / Reflux
  • 67
  • [ 10262-65-4 ]
  • [ 1195951-05-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: 1.42 h / 170 - 175 °C / microwave 3: ethanol / 20 h / 20 °C / Reflux
  • 68
  • [ 10262-65-4 ]
  • [ 1195951-09-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: 1.42 h / 170 - 175 °C / microwave 3: hydrogenchloride; hydrazine hydrate / 1,4-dioxane; methanol / Reflux 4: pyridine; copper diacetate / 1,2-dichloro-ethane / 24 h / 20 °C / Molecular sieve
  • 69
  • [ 10262-65-4 ]
  • [ 1195951-10-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: 1.42 h / 170 - 175 °C / microwave 3: hydrogenchloride; hydrazine hydrate / 1,4-dioxane; methanol / Reflux 4: pyridine; copper diacetate / 1,2-dichloro-ethane / 24 h / 20 °C / Molecular sieve 5: water; sodium hydroxide / tetrahydrofuran; methanol / 72 h / 20 °C
  • 70
  • [ 10262-65-4 ]
  • [ 1195951-06-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: 1.42 h / 170 - 175 °C / microwave 3: ethanol / 20 h / 20 °C / Reflux 4: water; lithium hydroxide / tetrahydrofuran; methanol / 16 h
  • 71
  • [ 10262-65-4 ]
  • [ 1195951-12-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: 1.42 h / 170 - 175 °C / microwave 3: hydrogenchloride; hydrazine hydrate / 1,4-dioxane; methanol / Reflux 4: pyridine; copper diacetate / 1,2-dichloro-ethane / 24 h / 20 °C / Molecular sieve 5: water; sodium hydroxide / tetrahydrofuran; methanol / 72 h / 20 °C 6: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 5 h / 20 °C 7: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 72
  • [ 10262-65-4 ]
  • [ 1195951-07-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: 1.42 h / 170 - 175 °C / microwave 3: ethanol / 20 h / 20 °C / Reflux 4: water; lithium hydroxide / tetrahydrofuran; methanol / 16 h 5: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 40 h / 20 °C
  • 73
  • [ 10262-65-4 ]
  • [ 1195951-11-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: 1.42 h / 170 - 175 °C / microwave 3: hydrogenchloride; hydrazine hydrate / 1,4-dioxane; methanol / Reflux 4: pyridine; copper diacetate / 1,2-dichloro-ethane / 24 h / 20 °C / Molecular sieve 5: water; sodium hydroxide / tetrahydrofuran; methanol / 72 h / 20 °C 6: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / acetonitrile / 5 h / 20 °C
  • 74
  • [ 10262-65-4 ]
  • [ 122-52-1 ]
  • C17H21O5P [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene at 20℃; for 24h; Sealed tube; Preparations of starting materials 1 and 3 General procedure: A sealed tube (35 mL) equipped with a stirring bar was loaded with 2-bromoethanones (1.0 mmol), then sodium benzenesulfinate (1.2 mmol) in DMF (20 mL) or phosphite (1.0 mmol) in toluene (20 mL) was added to the tube and the mixtures were stirred at room temperature till the 2-bromoethanones was totally consumed as indicated by TLC analysis (ca. 12 h for 1 and 24 h for 3). Then, the mixture was diluted with water (20 mL) and extracted with CH2Cl2 (30 mL x 3). Next, the organic phase was combined and dried over anhydrous Na2SO4. The solvent was removed by rotary evaporation and the oily mixture was purified with flash chromatograph column (elute: mixture of ethyl acetate and n-hexane), giving the desired products. And the 1H NMR spectra of the purified substrates were in accordance with the known literatures.
  • 75
  • [ 10262-65-4 ]
  • [ 1315483-07-8 ]
YieldReaction ConditionsOperation in experiment
98% With aluminum (III) chloride In benzene for 3h; Reflux;
  • 76
  • [ 10262-65-4 ]
  • 2-(6-hydroxynaphthalen-2-yl)-2-oxoethyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / benzene / 3 h / Reflux 2.1: potassium carbonate / acetonitrile / 0.33 h 2.2: 3 h
  • 77
  • [ 10262-65-4 ]
  • 2-(6-(((2,4-dinitrophenyl)sulfonyl)oxy)naphthalen-2-yl)-2-oxoethyl 4-(4-(bis(2-chloroethyl)amino)phenyl)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / benzene / 3 h / Reflux 2.1: potassium carbonate / acetonitrile / 0.33 h 2.2: 3 h 3.1: triethylamine; dmap / dichloromethane / 0.5 h / 0 °C
  • 78
  • [ 93-04-9 ]
  • [ 598-21-0 ]
  • [ 10262-65-4 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 2-Bromoacetyl bromide With aluminum (III) chloride In dichloromethane at 0℃; for 1h; Stage #2: 2-Methoxynaphthalene In dichloromethane at 0℃; for 5h;
  • 79
  • [ 10262-65-4 ]
  • (E)-6-acetyl-7,9-dihydroxy-2-(1-(((1-(2-(6-methoxynaphthalen-2-yl)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl)amino)ethylidene)-8,9b-dimethyldibenzo[b,d]furan-1,3 (2H,9bH)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium azide / acetone; water / 0 - 20 °C 2: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 20 °C
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 10262-65-4 ]

Aryls

Chemical Structure| 5471-35-2

[ 5471-35-2 ]

2-Bromo-1-(4-methoxynaphthalen-1-yl)ethanone

Similarity: 0.95

Chemical Structure| 28179-33-1

[ 28179-33-1 ]

2-Bromo-1-(4-phenoxyphenyl)ethanone

Similarity: 0.95

Chemical Structure| 5000-65-7

[ 5000-65-7 ]

2-Bromo-1-(3-methoxyphenyl)ethanone

Similarity: 0.95

Chemical Structure| 5471-35-2

[ 5471-35-2 ]

2-Bromo-1-(4-methoxynaphthalen-1-yl)ethanone

Similarity: 0.95

Chemical Structure| 28179-33-1

[ 28179-33-1 ]

2-Bromo-1-(4-phenoxyphenyl)ethanone

Similarity: 0.95

Bromides

Chemical Structure| 5471-35-2

[ 5471-35-2 ]

2-Bromo-1-(4-methoxynaphthalen-1-yl)ethanone

Similarity: 0.95

Chemical Structure| 28179-33-1

[ 28179-33-1 ]

2-Bromo-1-(4-phenoxyphenyl)ethanone

Similarity: 0.95

Chemical Structure| 5000-65-7

[ 5000-65-7 ]

2-Bromo-1-(3-methoxyphenyl)ethanone

Similarity: 0.95

Chemical Structure| 5471-35-2

[ 5471-35-2 ]

2-Bromo-1-(4-methoxynaphthalen-1-yl)ethanone

Similarity: 0.95

Chemical Structure| 28179-33-1

[ 28179-33-1 ]

2-Bromo-1-(4-phenoxyphenyl)ethanone

Similarity: 0.95

Ethers

Chemical Structure| 5471-35-2

[ 5471-35-2 ]

2-Bromo-1-(4-methoxynaphthalen-1-yl)ethanone

Similarity: 0.95

Chemical Structure| 5000-65-7

[ 5000-65-7 ]

2-Bromo-1-(3-methoxyphenyl)ethanone

Similarity: 0.95

Chemical Structure| 28179-33-1

[ 28179-33-1 ]

2-Bromo-1-(4-phenoxyphenyl)ethanone

Similarity: 0.95

Chemical Structure| 5471-35-2

[ 5471-35-2 ]

2-Bromo-1-(4-methoxynaphthalen-1-yl)ethanone

Similarity: 0.95

Chemical Structure| 5000-65-7

[ 5000-65-7 ]

2-Bromo-1-(3-methoxyphenyl)ethanone

Similarity: 0.95

Ketones

Chemical Structure| 5471-35-2

[ 5471-35-2 ]

2-Bromo-1-(4-methoxynaphthalen-1-yl)ethanone

Similarity: 0.95

Chemical Structure| 28179-33-1

[ 28179-33-1 ]

2-Bromo-1-(4-phenoxyphenyl)ethanone

Similarity: 0.95

Chemical Structure| 5000-65-7

[ 5000-65-7 ]

2-Bromo-1-(3-methoxyphenyl)ethanone

Similarity: 0.95

Chemical Structure| 5471-35-2

[ 5471-35-2 ]

2-Bromo-1-(4-methoxynaphthalen-1-yl)ethanone

Similarity: 0.95

Chemical Structure| 28179-33-1

[ 28179-33-1 ]

2-Bromo-1-(4-phenoxyphenyl)ethanone

Similarity: 0.95