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[ CAS No. 36854-57-6 ] {[proInfo.proName]}

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Chemical Structure| 36854-57-6
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Product Details of [ 36854-57-6 ]

CAS No. :36854-57-6 MDL No. :MFCD00018811
Formula : C10H11ClO Boiling Point : -
Linear Structure Formula :- InChI Key :QGXMHCMPIAYMGT-UHFFFAOYSA-N
M.W : 182.65 Pubchem ID :98173
Synonyms :

Calculated chemistry of [ 36854-57-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.82
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.17
Log Po/w (XLOGP3) : 3.3
Log Po/w (WLOGP) : 2.95
Log Po/w (MLOGP) : 2.69
Log Po/w (SILICOS-IT) : 3.18
Consensus Log Po/w : 2.86

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.22
Solubility : 0.109 mg/ml ; 0.000598 mol/l
Class : Soluble
Log S (Ali) : -3.33
Solubility : 0.0846 mg/ml ; 0.000463 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.8
Solubility : 0.0288 mg/ml ; 0.000158 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 36854-57-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 36854-57-6 ]

* 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 [ 36854-57-6 ]

[ 36854-57-6 ] Synthesis Path-Downstream   1~62

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  • [ 114793-37-2 ]
  • 4
  • [ 28710-97-6 ]
  • [ 36854-57-6 ]
  • 2-phenyl-butyric acid-(5-oxo-1-phenyl-2,5-dihydro-1<i>H</i>-pyrazol-3-ylamide) [ No CAS ]
  • 5
  • [ 39067-45-3 ]
  • [ 36854-57-6 ]
  • [ 113861-62-4 ]
  • 6
  • [ 36854-57-6 ]
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  • 7
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  • [ 115035-37-5 ]
  • 8
  • [ 90-27-7 ]
  • [ 36854-57-6 ]
YieldReaction ConditionsOperation in experiment
12.4 g (68%) With thionyl chloride;N,N-dimethyl-formamide; In dichloromethane; A) 2-Phenylbutyryl chloride Thionyl chloride (0.12 mol) in 60 mL of CH2 Cl2 was added to a stirred solution of 2-phenylbutyric acid (16.4 g, 0.10 mol). A catalytic amount of DMF was added and the reaction was allowed to continue overnight at room temperature. The volatiles were removed under vacuum and the residual liquid was vacuum distilled to yield 12.4 g (68%) of 2-phenylbutyryl chloride. IR (neat) 1798 cm-1 (C=O).
With thionyl chloride; at 20℃; for 24h;Inert atmosphere; General procedure: The corresponding carboxylic acid (1.5 mmol) was dissolved in SOCl2 (4 mmol) and stirred for 24 h at rt under nitrogen. After this period, the reaction mixture was concentrated in vacuum and diluted with anhydrous DCM (3 mL) under nitrogen. Then, the DCM solution of acid chloride was added to another RB flask containing the corresponding auxiliary (amine, 1 mmol) and Et3N (1.1 mmol) in anhydrous DCM (2 mL) at 0 C. Then, reaction mixture was stirred at rt for 10 min and then, the reaction mixture was refluxed for 12 h. After this period, the reaction mixture was diluted with DCM (5 mL) and washed with water followed by saturated aqueous NaHCO3 solution. The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuum and purification of the resulting reaction mixture by column chromatography (EtOAc/Hexanes=15:85) furnished the corresponding carboxamides (±)-1a-h, 1iB and 1j-(S).
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere; General procedure: To an oven-dried 100 mL three-necked flask, 4-phenylbutyric acid (1.6 g, 10 mmol), DMF (5drops) and DCM (20 mL) were added under a N2 atmosphere. Oxalyl chloride (1.0 mL, 12 mmol,1.2 equiv.) was added dropwise at 0 C resulting in vigorous bubbling. The mixture was stirred for 3h at room temperature, and the solvent was then removed in vacuo. The resulting acid chloride wasused immediately without further purification. To a solution of acid chloride in DCM(30 mL), thesolution of 8-amino-5-chroloquinoline (2.1 g, 12 mmol, 1.2 equiv.), Et3N (2.5 mL, 24 mmol, 2equiv.) in DCM (15 mL) were added dropwise to the solution at 0 C, and the solution was thenwarmed to room temperature. After stirring overnight, the reaction system was quenched with sat. aq.NaHCO3 (30 mL) and the organic layer was separated. The aqueous layer was extracted with DCM(2 x 15 mL). The combined organic layers were washed with 1 M HCl aq. (30 mL) and brine (30mL), dried over MgSO4, filtered and evaporated in vacuo. The resulting crude amide was purified bycolumn chromatography on silica gel (eluant: hexane/EtOAc = 4/1) to afford the desired amide as awhite solid (2.5 g, 77%).
With thionyl chloride; for 2h;Reflux; Example 125 2-Phenyl-2-ethyl-N-(4-methylbenzyl)-N-(1-methylpiperidin-4-yl)acetamide (47AKU-40) 2-Phenylbutyric acid (197 mg, 1.2 mmol) was dissolved in 2 ml thionylchloride and placed in 50 ml flask. Mixture was heated to reflux for 2 hrs and then concentrated on Rotavapor (50 C.).
With thionyl chloride; In toluene; at 115℃; for 16h; A mixture of 2-phenylbutanoic acid (2.0 g, 12.2 mmol) and 7 mL of thionyl chloride in 15 mL of toluene was heated at 115 C. for 16 hours. Concentration of the reaction mixture gave an oily residue. To this residue was added 10 mL of toluene and the resulting mixture was concentrated to yield a yellow oil. 1,1,2-tris(trimethylsilyloxy)ethane (8.0 mL, 24.4 mmol) was added to the yellow oil. The reaction mixture was heated at 100 C. for 16 hours under nitrogen atmosphere. At 50 C., 10 mL of dioxane and 2 mL of 1N HCl were added. The resulting mixture was stirred at 80 C. for 2 hours. Concentration of the mixture gave a yellow oily residue. 10 mL of water and 15 mL of diethyl ether were added. The organic layer was washed with 5 mL each of saturated sodium bicarbonate solution and brine, and dried over magnesium sulfate. The solid was removed via filtration. Concentration of the filtrate afforded the desired product (intermediate 57, 1.74 g, 80% yield) as a yellow oil, which was used for the next step without further purification. 1H NMR (400 MHz, CDCl3) delta 0.85 (t, J=7.2 Hz, 3H), 1.77-1.88 (m, 1H), 2.09-2.17 (m, 1H), 3.52 (t, J=7.2 Hz, 1H), 4.21 (d, J=4.9 Hz, 2H), 7.18-7.37 (m, 5H).
With thionyl chloride; for 2h;Heating / reflux; 2-Phenylbutyric acid (197 mg, 1.2 mmol) was dissolved in 2 ml thionylchloride and placed in 50 ml flask. Mixture was heated to reflux for 2 hrs and then concentrated on Rotavapor (50 C). The acid chloride (1.2 mmol) in 5 ml dichloromethane was added to 47AKU-5 (158 mg, 0.72 mmol) in 5 ml dichloromethane. After 20 hrs magnetic stirring the reaction mixture was concentrated on Rotavapor (40 C). Crude product was purified by flash chromatography (0-10% methanol in dichloromethane) giving 196 mg (74%) 47AKU-40. HCl-salt was prepared from 2M <n="148"/>HCl/diethylether in dichloromethane/heptane. TLC (10% methanol in dichloromethane): Rf =0.5. HPLC-MS (Method A): M+ =365.4 (UV/MS(%)=99/100). 1H-NMR (400 MHz5 CDCI3, rotamers): delta 7.32-6.98 (8H, m); 4.77 (IH5 bs); 4.50 (IH5 d); 4.29 (IH5 d); 3.43 and 3.21 (3H, 2m); 2.72 (2H, m); 2.62 (3H, s); 2.43 (IH5 m); 2.32 (3H5 s); 2.2 (3H5 m); 2.04 (2H5 m); 1.67 (3H, m); 0.92-0.72 (3H5 m). 13C-NMR (CDCl3): delta 174.7, 139.9, 137.3, 135.2, 129.7, 129.O5 127.8, 127.3, 125.8, 54.5, 51.6, 49.4, 46.0, 43.8, 28.9, 26.7, 26.3, 21.2, 12.7.
With thionyl chloride; at 25 - 70℃;Inert atmosphere; General procedure: To an oven-dried vial containing alpha-aryl carboxylic acid (1.2 equiv) was added SOCl2 neat(2.4 equiv) and the resuting mixture stirred at 25 C for 20 min then 70 : effluent gas flow is bubbled through a glass tube packed with powdered NaOH). The reaction was then concentrated in vacuo to afford the crude acid chloride, which was used in the next step without further purification.

Reference: [1]Tetrahedron Asymmetry,1998,vol. 9,p. 259 - 269
[2]Journal of the American Chemical Society,1948,vol. 70,p. 500
[3]Chemische Berichte,1934,vol. 67,p. 1617,1621
[4]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 399 - 404
[5]Journal of Organic Chemistry,1988,vol. 53,p. 882 - 884
[6]Journal of the American Chemical Society,1985,vol. 107,p. 5391
[7]Journal of Medicinal Chemistry,1980,vol. 23,p. 474 - 480
[8]Tetrahedron Asymmetry,1996,vol. 7,p. 1227 - 1234
[9]Journal of the American Chemical Society,2003,vol. 125,p. 4050 - 4051
[10]Journal of the American Chemical Society,2005,vol. 127,p. 5604 - 5607
[11]Patent: US5214191,1993,A
[12]Angewandte Chemie - International Edition,2009,vol. 48,p. 1636 - 1639
[13]Journal of the American Chemical Society,2009,vol. 131,p. 8344 - 8345
[14]Advanced Synthesis and Catalysis,2009,vol. 351,p. 3001 - 3009
[15]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2665 - 2667
[16]Journal of Medicinal Chemistry,2010,vol. 53,p. 6003 - 6017
[17]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 87 - 89
[18]Journal of the Chemical Society of Pakistan,2014,vol. 36,p. 462 - 472
[19]Journal of the American Chemical Society,2014,vol. 136,p. 13602 - 13605
[20]Tetrahedron,2015,vol. 71,p. 8333 - 8349
[21]Chemistry - A European Journal,2015,vol. 21,p. 16354 - 16358
[22]Chemistry Letters,2015,vol. 44,p. 1365 - 1367
[23]Patent: US2015/259291,2015,A1 .Location in patent: Paragraph 0660
[24]European Journal of Organic Chemistry,2017,vol. 2017,p. 2866 - 2870
[25]Patent: US2008/255192,2008,A1 .Location in patent: Page/Page column 22
[26]Patent: WO2007/124136,2007,A1 .Location in patent: Page/Page column 146-147
[27]Archiv der Pharmazie,2019,vol. 352
[28]Tetrahedron,2019,vol. 75,p. 4104 - 4109
[29]European Journal of Organic Chemistry,2020,vol. 2020,p. 937 - 943
[30]Angewandte Chemie - International Edition,2020,vol. 59,p. 5242 - 5247
    Angew. Chem.,2020,vol. 132,p. 5280 - 5285,6
  • 10
  • [ 36854-57-6 ]
  • [ 100-66-3 ]
  • [ 78423-10-6 ]
YieldReaction ConditionsOperation in experiment
100% aluminum (III) chloride; at 0 - 20℃; for 2h; <strong>[36854-57-6]2-Phenylbutyryl chloride</strong> (50.0 mL, 299 MMOL) was dissolved in anisole (75 mL) and cooled to 0C. AICI3 (40.377 g, 303 MMOL) was added portionwise and the resulting mixture allowed to warm to RT then stirred for 2 h. Ice was added portionwise followed by H20 (100 mL). The mixture was extracted with CH2CI2 (3 x 100 mL) and the combined organics dried (MGS04) and concentrated. The residue was distilled to remove the remaining ANISOLE (1 mm Hg, 40-55 C) to provide 2 (77.27 g, 100%) as a tan OIL. H NMR (400 MHz, CDCI3) : 6 0.90 (t, J= 7.5 Hz, 3H), 1. 85 (dq, 1H), 2.18 (dq, 1H), 3.81 (s, 3H), 4.40 (t, J= 7.2 Hz, 1H), 6.85 (d, J= 5.0 Hz, 2H), 7.19 (m, 1H), 7.28 (m, 4H), 7.95 (d, J= 5.0 Hz, 2H). Step 2: 1- [4- (DIETHOXYMETHYL) PHENYL]-1- (4-METHOXYPHENYL)-2-PHENYLBUTAN-1-OL (D Magnesium turnings (9.64 g, 397 MMOL) were heated to 160 C under vacuum for 2 hours, then were cooled to RT under nitrogen. THF (400 mL) was added followed by portionwise addition of 4-bromobenzaldehyde diethyl acetal (80.0 mL, 393 MMOL). The mixture was heated with a heat gun to initiate the reaction, then allowed to stir at RT (while gently refluxing) for 90 min. The resulting dark red solution was cooled to 0 C and a solution of 2 (77.27 g, 304 MMOL) in THF (50 mL) was added. The mixture was stirred at RT for 3 hours. Saturated aqueous NH4CI (150 mL) and H20 (150 mL) were added and the two layers were separated. The aqueous layer was extracted with ET20 (3 x 100 mL), and the combined organics were dried (MGS04) and concentrated to provide 3 as a light yellow oil that was carried on without further PURIFICATION. H NMR (400 MHz, CDCI3) : 8 0.72 (t, J= 7.3 Hz, 3H), 1.25 (t, J= 7.0 Hz, 6H), 1.77 (q, J= 7.3 Hz, 2H), 2.35 (s, 1H), 3.69 (s, 3H), 3.52-3. 65 (m, 5H), 5.50 (s, 1H), 6.62 (d, J= 8.8 Hz, 2H), 7.08 (m, 1H), 7.12 (m, 6H), 7.44 (d, J= 8.2 Hz, 2H), 7.53 (d, J= 8. 2 Hz, 2H). Step 3: 4-11-(4-METHOXYPHENYL)-2-PHENYLBUT-1-ENYLIBENZALDEHYDE ( A solution of compound 3 (163.09 g, 375 MMOL) in ETOH (750 mL) was charged with concentrated aqueous HCI (150 mL) and the resulting solution heated at 80 C for 90 min. The solution was allowed to cool to RT and then was concentrated to the aqueous layer. H20 (500 mL) was added and the mixture extracted with CH2CI2 (3 x 150 mL). The combined organic layers were dried (MGS04) and concentrated to provide 4 (119.78 g, 93% over 2 steps) as a brown oil (3 : 1 mixture OF Z : E isomers). The mixture was carried on without further purification. Z-isomer : H NMR (400 MHz, CDCI3) : 8 0.94 (t, J= 7.5 Hz, 3H), 2.45 (q, J= 7.5 Hz, 2H), 3.68 (s, 3H), 6.56 (d, J= 8.6 Hz, 2H), 6.75 (d, J= 8.6 Hz, 2H), 7.08-7. 21 (m, 5H), 7.41 (d, J= 8.1 Hz, 2H), 7.87 (d, J= 8.1 Hz, 2H), 10.02 (s, 1H). E-isomer : H NMR (CDCI3) : No. 0.97 (t, J= 7.4 Hz, 3H), 2.52 (q, 7. 4 HZ, 2H), 3.83 (s, 3H), 6.90 (d, J= 8. 3 Hz, 2H), 7.03 (d, J= 8. 3 Hz, 2H), 7.0-8-7. 21 (m, 7H), 7.51 (d, J= 8.1 Hz, 2H), 9. 83 (s, 1 H). Step 4: Ethyl (2E)-3- {4-[(1Z)-1-(4-methoxyphenyl)-2-phenylbuten-1- ENYL] PROP-2-ENOATE (O Compound 4 was dissolved in CH3CN (700 mL) and triethyl phosphonoacetate (88.5 mL, 446 MMOL) added followed by LiCI (29.794 g, 703 MMOL) and DBU (60.0 mL, 401 MMOL). The mixture was allowed to stir at RT for 90 minutes then concentrated. H20 (500 mL) was added and the mixture extracted with CH2CI2 (3 x 150 mL). The combined organics were dried (MGS04) and concentrated. The residue was recrystallized from hexanes to provide 5 (39.80 g, 32%) as pale yellow needles in a 98: 2 ratio of Z: E isomers NMR (400 MHz, CDCI3) : No. 0.94 (t, J= 7.4 Hz, 3H), 1.35 (t, J= 7.2 Hz, 3H), 2.47 (q, J= 7.4 Hz, 2H), 3.68 (s, 3H), 4.27 (q, J= 7.2 Hz, 2H), 6.43 (d, J= 16.0 Hz, 1H), 6.55 (d, J= 8. 8 Hz, 2H), 6.76 (d, J= 8.8 Hz, 2H), 7.11-7. 20 (m, 5H), 7.26 (d, J= 8. 3 Hz, 2H), 7.51 (d, J= 8. 3 Hz, 2H), 7.70 (d, J= 16.0 Hz, 1H). Step 5 : (2E)-3-{4-[(1Z)-1-(4-Methoxyphenyl)-2-phenylbut-1-enyl]phenyl}prop-2- enoic acid ( Compound 5 (39. 80 g, 96.5 MMOL) was dissolved in ETOH (300 mL) and THF (300 mL). 1 M aqueous NAOH (250 mL, 250 MMOL) was added and the solution refluxed for 2 h. The reaction was cooled to RT and then acidified to pH 2 with 6N aq. HCI. H2O (750 mL) and CH2CI2 (500 mL) were added and the two layers were separated. The aqueous layer was extracted with CH2CI2 (2 x 100 mL). The combined organics were dried (Na2SO4) and concentrated to provide the title compound, 6 (39. 34 g, 100%), as a pale YELLOW SOLID. H NMR (400 MHz, DMSO-D6) : 8 0.95 (t, J= 7.4 Hz, 3H), 2.48 (q, J= 7.4 Hz, 2H), 3.69 (s, 3H), 6.46 (d, J= 15.8 Hz, 1H), 6.56 (d, J= 8. 6 Hz, 2H), 6.77 (d, J= 8.6 Hz, 2H), 7.10-7. 12 (m, 3H), 7.13-7. 19 (m, 2H), 7.28 (d, J= 8. 3 HZ, 2H), 7.54 (d, J= 8. 3 Hz, 2H), 7.80 (d, J= 15. 8 Hz, 1H). Step 6: (2-3- {4- [ (1-1- (4-HYDROXYPHENYL)-2-PHENYLBUT-1-ENYL] PHENYL} prop-2- enoic acid (1, Compound 1) Compound 6 (10.30 g, 26.8 MMOL) was dissolved in CH2CI2 (250 mL) and cooled to 0 C under N2. BBR3 (7.50 mL, 79.3 MMOL) was added dropwise and the resulting solution was allo...
76% With aluminum (III) chloride; In dichloromethane; at 0 - 20℃; for 2.5h; General procedure: Friedel-Crafts acylation was performed modifying known procedures [1-3]. A mixture of AlCl3 (1.2 eq) and anisole (1.1 eq) in anh. DCM was stirred and subsequently cooled to 0 C. The re-spective acylchloride (1 eq) was added dropwise whereupon the suspension turned orange and clear. The mixture was warmed to rt and was stirred for further 2.5 h. The reaction was cooled to 0 C again and diluted with water. The organic phase was separated and the aqueous phase ex-tracted 3× with DCM. The combined organic extracts were washed with brine, dried over anh. Na2SO4, filtered and evaporated to dryness. Purification was carried out by crystallization.1-(4-Methoxyphenyl)-2-phenylbutan-1-one (8a)4.37 g of AlCl3 (27.37 mmol) and 3.26 g of anisole (30.11 mmol) were suspended in 35 mL anh. DCM 5.0 g of <strong>[36854-57-6]2-phenylbutyryl chloride</strong> 7a (27.37 mmol) were added. Crystallization from cold ethanol afforded 8a as a white powder (5.32 g, 20.92 mmol, 76%). 1H-NMR: (200 MHz, CDCl3): delta 0.90 (t, 3J= 7.4 Hz, 3H, CHCH2CH3), 1.74 - 1.96 (m, 1H, CH2CH3), 2.09 - 2.31 (m, 1H, CHCH2CH3), 3.83 (s, 3H, OCH3), 4.41 (t, 3J= 7.3 Hz, 1H, CHCH2CH3), 6.87 (d, 3J= 9.0 Hz, 2H, ArH), 7.15 - 7.34 (m, 5H, ArH), 7.97 (d, 3J= 9.0 Hz, 2H, ArH).
  • 12
  • [ 36854-57-6 ]
  • [ 4402-32-8 ]
  • [ 101745-21-5 ]
YieldReaction ConditionsOperation in experiment
With benzene
  • 14
  • [ 36854-57-6 ]
  • [ 99306-87-3 ]
  • [ 99306-86-2 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran for 25h; Ambient temperature;
  • 15
  • [ 36854-57-6 ]
  • [ 1519-21-7 ]
  • 16
  • [ 36854-57-6 ]
  • [ 1711-06-4 ]
  • [ 108796-49-2 ]
  • 17
  • [ 36854-57-6 ]
  • [ 15118-60-2 ]
  • 4-[4-(2-Phenyl-butyrylamino)-phenyl]-butyric acid [ No CAS ]
  • 18
  • [ 36854-57-6 ]
  • [ 50547-51-8 ]
  • [ 6761-31-5 ]
  • 19
  • [ 36854-57-6 ]
  • [ 50547-51-8 ]
  • 2-ethyl-3-[di(2-phenylbutyryl)amino]quinazolin-4(3H)-one [ No CAS ]
  • 21
  • [ 36854-57-6 ]
  • [ 4356-66-5 ]
  • [ 762-42-5 ]
  • 4-benzyl-8-ethyl-5-methyl-8-phenyl-4,8-dihydro-1-oxa-7-thia-4-aza-azulene-2,3-dicarboxylic acid dimethyl ester [ No CAS ]
  • 22
  • [ 36854-57-6 ]
  • 5-(2-acetoxy-ethyl)-3,4-dimethyl-thiazolium; iodide [ No CAS ]
  • [ 762-42-5 ]
  • 6-(2-acetoxy-ethyl)-8-ethyl-4,5-dimethyl-8-phenyl-4,8-dihydro-1-oxa-7-thia-4-aza-azulene-2,3-dicarboxylic acid dimethyl ester [ No CAS ]
  • 23
  • [ 36854-57-6 ]
  • [ 28048-27-3 ]
  • [ 762-42-5 ]
  • 4-benzyl-8-ethyl-5,6-dimethyl-8-phenyl-4,8-dihydro-1-oxa-7-thia-4-aza-azulene-2,3-dicarboxylic acid dimethyl ester [ No CAS ]
  • 24
  • [ 36854-57-6 ]
  • [ 762-42-5 ]
  • 3-butyl 4-methylthiazolium bromide [ No CAS ]
  • 4-butyl-8-ethyl-5-methyl-8-phenyl-4,8-dihydro-1-oxa-7-thia-4-aza-azulene-2,3-dicarboxylic acid dimethyl ester [ No CAS ]
  • 25
  • 3-ethyl-4,5-dimethylthiazol-3-ium bromide [ No CAS ]
  • [ 36854-57-6 ]
  • [ 762-21-0 ]
  • 4,8-diethyl-5,6-dimethyl-8-phenyl-4,8-dihydro-1-oxa-7-thia-4-aza-azulene-2,3-dicarboxylic acid diethyl ester [ No CAS ]
  • 26
  • [ 201230-82-2 ]
  • [ 36854-57-6 ]
  • [ 615-43-0 ]
  • 2-(1-phenylpropyl)-4H-benzo[d][1,3]oxazin-4-one [ No CAS ]
  • 27
  • [ 201230-82-2 ]
  • [ 36854-57-6 ]
  • [ 63069-48-7 ]
  • 6-chloro-2-(1-phenylpropyl)-4H-3,1-benzoxazin-4-one [ No CAS ]
  • 28
  • [ 201230-82-2 ]
  • [ 36854-57-6 ]
  • [ 33348-34-4 ]
  • 6-cyano-2-(1-phenylpropyl)-4H-3,1-benzoxazin-4-one [ No CAS ]
  • 29
  • [ 57907-49-0 ]
  • [ 36854-57-6 ]
  • C20H19NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine In tetrahydrofuran; dichloromethane for 24h;
  • 31
  • [ 36854-57-6 ]
  • [ 150986-82-6 ]
  • N-(3-cyano-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl)-2-phenylbutyramide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate; In diethyl ether; at 20℃; for 24h; Example 18 N-(3-Cyano-4,7-dihydro-5H-thieno [2,3-c]pyran-2-yl)-2-phenyl-butyramide To a stirred suspension of 2-Amino-3-cyano-4,7-dihydro-5H-thieno [2,3-c]pyran (361 mg; 2.0 mmol; prepared as described in Example 2, Step 1) and potassium carbonate (1.40 g; 10.1 mmol) in diethylether (6.0 ML) was added <strong>[36854-57-6]2-phenylbutyryl chloride</strong> dropwise.The resulting mixture was stirred at room temperature for 24 h.The solvent was then removed in vacuo, the residue taken up into methylene chloride and washed with water.The organic layer was dried (sodium sulfate) filtered and concentrated in vacuo to give crude product which was triturated with diethyl ether to provide 428 mg (66%) of N-(3-Cyano-4,7-dihydro-5H-thieno[2,3-c]pyran-2-yl)-2-phenyl-butyramide as a beige colored solid. EI-HRMS m/e calcd for C18H18N2O2S (M+) 326.1809, found 326.1809.
  • 32
  • [ 36854-57-6 ]
  • [ 6638-79-5 ]
  • [ 166337-42-4 ]
YieldReaction ConditionsOperation in experiment
98% With pyridine; In tetrahydrofuran; dichloromethane; at 0 - 20℃; To a suspension of 60% NaH in mineral oil (12.7 g, 31.8 MMOL) in anhydrous THF (300 mL) at 0 C was added 4-bromophenol (50.0 g, 28.9 MMOL) dissolved in THF (100 mL) dropwise over 1 h. The reaction mixture was stirred at 0 C for 30 min, and chloromethylmethyl ether (24.8 mL, 32.6 MMOL) dissolved in THF (30 mL) was added dropwise over 20 min. The reaction mixture was stirred overnight at RT. H20 (250 mL) was added, and the mixture was extracted with ET20 (2 x 250 mL). The combined ethereal extracts were washed with brine (500 mL), dried over MGS04, and concentrated. The residue was distilled under vacuum to afford 57.6 g (92%) of 13 as a colorless OIL. H NMR (400 MHz, DMSO-D6) : No. 3.33 (s, 3H), 5.15 (s, 2H), 6.96 (d, J = 9. 0 HZ, 2H), 7.43 (d, J = 9. 0 HZ, 2H). Step 2: N-METHOXY-N-METHYL-2-PHENYLBUTANAMIDE (14 To a stirred solution of pyridine (33.1 mL, 40.9 MMOL) and N, O- dimethylhydroxylamine hydrochloride (26.0 g, 26.7 MMOL) in anhydrous CH2CI2 (300 mL) at 0 C was added dropwise <strong>[36854-57-6]2-phenylbutyryl chloride</strong> (37.4 g, 20.5 MMOL) dissolved in THF (100 mL). The reaction mixture was stirred overnight at RT. H20 (300 mL) was added, and the mixture was extracted with CH2CI2 (2 x 200 mL). The combined extracts were washed successively with 5% aqueous HCI (300 mL), 5% aqueous NAHC03 (300 mL), H20 (300 mL), and brine (300 mL). The mixture was dried over NA2SO4, filtered, and concentrated to afford 41.6 g (98%) of 14 as a colorless oil which was used without further purification.'HNMR (400 MHz, CDCI3) : 8 0.87 (t, J = 7. 3 Hz, 3H), 1.74 (h, J = 7. 1 Hz, 1H), 2. 08 (h, J = 7. 1 Hz, 1H), 3.14 (s, 3H), 3.46 (s, 3H), 3. 88 (br s, 1H), 7.19-7. 33 (m, 5H). Step 3-1- [4- (METHOXYMETHOXY) PHENYL]-2-PHENYLBUTAN-1-ONE (J 5 To a stirred solution of 13 (99.0 g, 0.46 mol) in anhydrous THF (750 mL) was added n-BuLi (1.6 M in hexanes, 310 mL, 0.50 mol) dropwise at-78 C. The reaction mixture was stirred for 30 min and 14 (90.1 g, 0.43 mol) dissolved in THF (500 mL) was added dropwise. The reaction mixture was stirred at-78 C for 1 h and then slowly warmed to 0 C. H20 (500 mL) was added and the volatiles were removed under reduced pressure. The residue was extracted with ET20 (3 x 500 mL) and the combined extracts were washed with water (500 mL) and brine (500 mL). The mixture was dried over MGS04 and concentrated. The residue was recrystallized from hexanes to afford 97.6 g (80%) of 15 as white needles.'HNMR (400 MHz, DMSO-d6) : 8 0. 79 (t, J = 7. 3 Hz, 3H), 1.68 (h, J = 7. 0 HZ, 1 H), 2.03 (h, J = 7. 0 Hz, 1H), 3.32 (s, 3H), 4.65 (t, J=7. 3HZ, 1H), 5.21 (s, 2H), 7.03 (d, J=8. 8HZ, 2H), 7.15 (t, J = 7. 1 Hz, 1H), 7.23-7. 30 (m, 4H), 7.98 (d, J=8. 8HZ, 2H). Step 4: 1- [4- (DIETHOXYMETHYL) PHENYL]-1- [4- (METHOXYMETHOXY) PHENYL]-2- PHENYLBUTAN-1-OL () To a stirred solution of 4-bromobenzaldehyde diethyl acetal (107 g, 0.41 mol) in anhydrous THF (750 mL) was added n-BuLi (1.6 M in hexanes, 268 mL, 0.43 mol) dropwise at-78 C. After stirring for 1 h at-78 C, a solution of 15 (97.6 g, 0.34 mol) in THF (750 mL) was cannulated into the reaction mixture portionwise. The mixture was stirred overnight at RT, H20 (500 mL) was added, and the volatiles were removed under reduced pressure. The residue was extracted with ET20 (3 x 500 mL) and the combined extracts washed with H20 (500 mL) and brine (500 mL). The mixture was dried over MGS04 and concentrated to afford 194 g of 16 that was used without further purification.'HNMR (400 MHz, DMSO-d6) : 8 0.58 (t, J = 7.3 Hz, 3H), 1.12 (m, 6H), 1.52 (m, 1H), 1.70 (m, 1 H), 3.23 (s, 3H), 3.40-3. 65 (m, 5H), 4.98 (s, 2H), 5.41 (s, 1H), 5.51 (s, 1H), 6.62 (d, J = 8.8 Hz, 2H), 6.96-7. 06 (m, 3H), 7.17- 7.23 (m, 4H), 7.31 (d, J = 8.0 Hz, 2H), 7.61 (d, J = 8.4 Hz, 2H). Step 5: 4- [ (1)-1- (4-HYDROXYPHENYL)-2-PHENYLBUT-1-ENYL] BENZALDEHYDE (10 To a solution of 16 (194 g, 0.42 mol) in ETOH (1.25 L) was added 12 M HCI (250 mL). The reaction mixture was refluxed for 3 h, cooled to RT, and the volatiles were removed under reduced pressure. H2O (750 mL) was added and the mixture was extracted with ether (3 x 500 mL). The combined ethereal extracts were washed with H20 (750 mL), brine (750 mL), and dried over MGS04. CONCENTRATION followed by recrystallization from hexanes afforded 52.8 g (38%) of 10 as a white solid.'HNMR (400 MHz, DMSO-d6) : 8 0.83 (t, J = 7.3 Hz, 3H), 2.33 (q, J = 7.3 Hz, 2H), 6.40 (d, J = 8. 4 Hz, 2H), 6.60 (d, J = 8.4 Hz, 2H), 7.10-7. 20 (m, 5H), 7.40 (d, J = 7.9 Hz, 2H), 7.90 (d, J = 8. 1 Hz, 2H), 9.23 (s, 1H), 9.98 (s, 1H). Step 6: TERT-BUTYL (2E)-3- (4- [ (121-1- (4-HYDROXYPHENYL)-2-PHENYLBUT-L- enyl] phenyl} prop-2-enoate (12 To a stirred solution of (TERT-BUTOXYCARBONYLMETHYLENE) triphenylphosphorane (5.19 g, 13.8 MMOL) in CH2CI2 (200 mL) was added 10 (2.29 g, 7.0 MMOL) dissolved in CH2CI2 (100 mL) dropwise at 0 C. The reaction mixture was stirred at RT for 2 h. Silica gel (12.0 g) was added, and the volatiles were removed under reduced pressure. Flash chromatography (20: 1 to 4: 1 hexane: Et...
  • 33
  • [ 93071-82-0 ]
  • [ 36854-57-6 ]
  • N-(2-fluoro-5-methylbenzyl)-2-phenylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20.0℃; for 0.5h; Example 1-2 N-(2-fluoro-5-methylbenzyl)-2-phenylbutanamide (1-2) A solution of <strong>[93071-82-0](2-fluoro-5-methylphenyl)methanamine</strong> (1-f, 50 mg, 0.26 mmol, Oakwood Products, Inc., West Columbia, S.C.) and diisopropylethylamine (88 uL, 0.52 mmol) in dichloromethane (1 mL) was treated at room temperature with 2-phenylbutanoyl chloride (1-a, 47 mg, 0.26 mmol). The reaction mixture was stirred for 30 min, partitioned between dichloromethane and 0.1N-NaOH. The aqueous layer was removed and the organic layer was washed with 0.1N-HCl. The aqueous layer was removed by filtering through a plastic frit. The organic layer was evaporated in vacuo to give the desired product (1-2); HRMS (M+1) 286.1586. Additionally, Examples 1-3 through 1-28 in Table 1 below were prepared by the general protocols described in Scheme 1. Specific details of the synthesis of particular compounds are presented below. Examples 1-6 through 1-9 were obtained by direct introduction of ethyl, vinyl or cyclopropyl group to the corresponding bromide (1-4 or 1-15) by a protocol shown in Scheme 2 (1-6 and 1-7) or known synthetic methods disclosed in Weichert, A. et al., Synlett 1996, 473, and Krolski, M. E., et al. J. Org. Chem. 1988, 53, 1171 (1-8 and 1-9). The 2-arylbutanoic acid portion in the compounds of Examples 1-10, 1-11, 1-16 and 1-17 was prepared by alkylation (lithium diisopropylamide; ethyl iodide) of the corresponding ethyl arylacetate followed by the hydrolysis (KOH in MeOH).
  • 34
  • [ 69097-20-7 ]
  • [ 36854-57-6 ]
  • [ 1067187-83-0 ]
YieldReaction ConditionsOperation in experiment
A mixture of 2-phenylbutanoic acid (2.0 g, 12.2 mmol) and 7 mL of thionyl chloride in 15 mL of toluene was heated at 115 C. for 16 hours. Concentration of the reaction mixture gave an oily residue. To this residue was added 10 mL of toluene and the resulting mixture was concentrated to yield a yellow oil. 1,1,2-tris(trimethylsilyloxy)ethane (8.0 mL, 24.4 mmol) was added to the yellow oil. The reaction mixture was heated at 100 C. for 16 hours under nitrogen atmosphere. At 50 C., 10 mL of dioxane and 2 mL of 1N HCl were added. The resulting mixture was stirred at 80 C. for 2 hours. Concentration of the mixture gave a yellow oily residue. 10 mL of water and 15 mL of diethyl ether were added. The organic layer was washed with 5 mL each of saturated sodium bicarbonate solution and brine, and dried over magnesium sulfate. The solid was removed via filtration. Concentration of the filtrate afforded the desired product (intermediate 57, 1.74 g, 80% yield) as a yellow oil, which was used for the next step without further purification. 1H NMR (400 MHz, CDCl3) delta 0.85 (t, J=7.2 Hz, 3H), 1.77-1.88 (m, 1H), 2.09-2.17 (m, 1H), 3.52 (t, J=7.2 Hz, 1H), 4.21 (d, J=4.9 Hz, 2H), 7.18-7.37 (m, 5H).
  • 35
  • [ 36854-57-6 ]
  • [ 89109-17-1 ]
  • [ 929612-71-5 ]
YieldReaction ConditionsOperation in experiment
85% Synthesis Example 39 4-Hydroxy-1-phenyl-3-(2-phenylbutyryl)-1,8-naphthyridin-2(1H)-one; (i) In accordance with a process described in JP-61-246183A, 4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one was synthesized. To a suspension of the synthesized compound (1.19 g, 5.0 mmol) in DMF (40 mL) was added sodium hydride (purity of about 60%, 200 mg, 5.0 mmol, 1.0 eq.). The mixture was stirred until no more hydrogen was generated, to obtain a solution. Then, <strong>[36854-57-6]2-phenylbutyryl chloride</strong> (0.92 mL, 5.5 mmol, 1.1eq.) was added thereto, and the mixture was stirred at a room temperature for 1 hour. To the mixture was added a saturated sodium hydrogencarbonate aqueous solution, and the resulting precipitate was separated by filtration, washed with water, and dried to give 1-phenyl-4-(2-phenylbutyryloxy) -1, 8-naphthyridin-2 (1H) -one as a form of crystal (1.63 g, yield 85%). mp: 166-168C 1H NMR (CDCl3) delta: 1.04 (3H, t, J=7.6Hz), 1.92-20.8 (1H, m), 2.22-2.38 (1H, m), 3.85 (1H, t, J=7.6Hz), 6.68 (1H, s), 6.98 (1H, dd, J=4.6Hz, 7.9Hz), 7.23-7.26 (2H, m), 7.33-7.59 (9H, m), 8.40 (1H, dd, J=1.6Hz, 4.6Hz)
  • 36
  • [ 36854-57-6 ]
  • [ 932-32-1 ]
  • [ 1188327-74-3 ]
  • 37
  • [ 4812-20-8 ]
  • [ 36854-57-6 ]
  • [ 1218772-84-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 40℃; for 16h; Inert atmosphere;
  • 38
  • [ 36854-57-6 ]
  • [ 30018-16-7 ]
  • [ 38701-07-4 ]
  • 39
  • [ 535-52-4 ]
  • [ 36854-57-6 ]
  • [ 1386996-23-1 ]
  • 40
  • [ 36854-57-6 ]
  • [ 367-24-8 ]
  • [ 349431-99-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-bromo-2-fluoroaniline With triethylamine In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-Phenylbutyryl chloride In dichloromethane for 17h; Inert atmosphere;
  • 41
  • [ 36854-57-6 ]
  • [ 2401-24-3 ]
  • C17H18ClNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-chloro-5-methoxyaniline With triethylamine In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-Phenylbutyryl chloride In dichloromethane for 17h; Inert atmosphere;
  • 42
  • [ 36854-57-6 ]
  • [ 363-81-5 ]
  • [ 1386996-22-0 ]
  • 43
  • [ 36854-57-6 ]
  • [ 2847-57-6 ]
  • [ 16282-16-9 ]
  • [ 1118-46-3 ]
YieldReaction ConditionsOperation in experiment
25% With indium; In neat (no solvent); at 80℃; for 0.25h;Inert atmosphere; Sonication; General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water-detergent bath at 60 C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70%; output power = 70%) for 10 min. After addition of 10% (m/v) solution of No.18 NaOH (2 mL) and 10 muL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90% recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 A, 70-230 mesh) doped with 10% of KF (hexanes/DCM 8:2) gave 0.096 g (53%) of 3fa as a colorless oil.
  • 44
  • [ 36854-57-6 ]
  • [ 68971-88-0 ]
  • 2-phenyl-1-(3-methylphenyl)butan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With indium; In neat (no solvent); at 80℃; for 6h;Inert atmosphere; Sonication; General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water-detergent bath at 60 C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70%; output power = 70%) for 10 min. After addition of 10% (m/v) solution of No.18 NaOH (2 mL) and 10 muL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90% recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 A, 70-230 mesh) doped with 10% of KF (hexanes/DCM 8:2) gave 0.096 g (53%) of 3fa as a colorless oil.
  • 45
  • [ 36854-57-6 ]
  • [ 62942-25-0 ]
  • [ 1422446-26-1 ]
YieldReaction ConditionsOperation in experiment
61% With indium; In neat (no solvent); at 80℃; for 7h;Inert atmosphere; Sonication; General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water-detergent bath at 60 C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70%; output power = 70%) for 10 min. After addition of 10% (m/v) solution of No.18 NaOH (2 mL) and 10 muL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90% recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 A, 70-230 mesh) doped with 10% of KF (hexanes/DCM 8:2) gave 0.096 g (53%) of 3fa as a colorless oil.
  • 46
  • (2,6-dimethylphenyl)trimethylstannane [ No CAS ]
  • [ 36854-57-6 ]
  • [ 1422446-27-2 ]
YieldReaction ConditionsOperation in experiment
75% With indium; In neat (no solvent); at 20℃; for 32h;Inert atmosphere; Sonication; General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water-detergent bath at 60 C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70%; output power = 70%) for 10 min. After addition of 10% (m/v) solution of No.18 NaOH (2 mL) and 10 muL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90% recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 A, 70-230 mesh) doped with 10% of KF (hexanes/DCM 8:2) gave 0.096 g (53%) of 3fa as a colorless oil.
  • 47
  • [ 36854-57-6 ]
  • [ 960-16-7 ]
  • [ 16282-16-9 ]
  • [ 1461-22-9 ]
YieldReaction ConditionsOperation in experiment
84% With indium; In neat (no solvent); at 80℃; for 0.833333h;Inert atmosphere; Sonication; General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water-detergent bath at 60 C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70%; output power = 70%) for 10 min. After addition of 10% (m/v) solution of No.18 NaOH (2 mL) and 10 muL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90% recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 A, 70-230 mesh) doped with 10% of KF (hexanes/DCM 8:2) gave 0.096 g (53%) of 3fa as a colorless oil.
  • 48
  • [ 36854-57-6 ]
  • [ 31614-66-1 ]
  • [ 217823-67-1 ]
YieldReaction ConditionsOperation in experiment
76% With indium; In neat (no solvent); at 80℃; for 3h;Inert atmosphere; Sonication; General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water-detergent bath at 60 C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70%; output power = 70%) for 10 min. After addition of 10% (m/v) solution of No.18 NaOH (2 mL) and 10 muL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90% recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 A, 70-230 mesh) doped with 10% of KF (hexanes/DCM 8:2) gave 0.096 g (53%) of 3fa as a colorless oil.
  • 49
  • [ 36854-57-6 ]
  • [ 68971-87-9 ]
  • 2-phenyl-1-(2-methylphenyl)butan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With indium; In neat (no solvent); at 80℃; for 3h;Inert atmosphere; Sonication; General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water-detergent bath at 60 C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70%; output power = 70%) for 10 min. After addition of 10% (m/v) solution of No.18 NaOH (2 mL) and 10 muL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90% recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 A, 70-230 mesh) doped with 10% of KF (hexanes/DCM 8:2) gave 0.096 g (53%) of 3fa as a colorless oil.
  • 50
  • [ 36854-57-6 ]
  • [ 6452-61-5 ]
  • [ 16282-16-9 ]
  • [ 683-18-1 ]
YieldReaction ConditionsOperation in experiment
52% With indium; In neat (no solvent); at 80℃; for 0.5h;Inert atmosphere; Sonication; General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water-detergent bath at 60 C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70%; output power = 70%) for 10 min. After addition of 10% (m/v) solution of No.18 NaOH (2 mL) and 10 muL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90% recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 A, 70-230 mesh) doped with 10% of KF (hexanes/DCM 8:2) gave 0.096 g (53%) of 3fa as a colorless oil.
  • 51
  • [ 36854-57-6 ]
  • Dibutylbis(3-methylphenyl)stannane [ No CAS ]
  • 2-phenyl-1-(3-methylphenyl)butan-1-one [ No CAS ]
  • [ 683-18-1 ]
YieldReaction ConditionsOperation in experiment
61% With indium; In neat (no solvent); at 80℃; for 0.25h;Inert atmosphere; Sonication; General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water-detergent bath at 60 C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70%; output power = 70%) for 10 min. After addition of 10% (m/v) solution of No.18 NaOH (2 mL) and 10 muL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90% recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 A, 70-230 mesh) doped with 10% of KF (hexanes/DCM 8:2) gave 0.096 g (53%) of 3fa as a colorless oil.
  • 52
  • [ 36854-57-6 ]
  • [ 62967-77-5 ]
  • [ 1422446-26-1 ]
  • [ 683-18-1 ]
YieldReaction ConditionsOperation in experiment
42% With indium; In neat (no solvent); at 80℃; for 0.166667h;Inert atmosphere; Sonication; General procedure: In a flame dried Schlenk tube (fitted with a Teflon plug valve) 1.2 mmol (0.127 g) of No.15 butanoyl chloride (2a) was added to a stirred mixture of 1.0 mmol (0.402 g) of No.16 tributyl(3-chlorophenyl)stannane (1f) and No.17 indium powder (0.148 g, 1.0 mmol) under a nitrogen gas stream. After purging the system with nitrogen by means of three pump-fill cycles, the tube was capped and immersed in a water-detergent bath at 60 C. The ultrasonic titanium horn was placed into the bath to a distance of 10 mm to the wall and 5 mm from the bottom of the Schlenk tube and ultrasound was applied in a pulsed mode (duty cycle = 70%; output power = 70%) for 10 min. After addition of 10% (m/v) solution of No.18 NaOH (2 mL) and 10 muL of No.19 tetradecane (internal standard), the mixture was stirred at room temperature for 15 min and then diluted with DCM (5 mL). Once the stirring was stopped for about 5 min, the supernatant liquid mixture was decanted into a separatory funnel. The silvery-white solid, settled at the bottom of the Schlenk tube, was washed with acetone (2 × 5 mL), deionized water (2 × 5 mL), and then vacuum-dried at room temperature. As indicated by DSC analysis, the dried sample (0.133 g) meant a 90% recovered yield of pure No.20 indium. On the other hand, the organic phase was successively washed with water and brine, dried over Na2SO4, filtered, analyzed by GC, and then concentrated in vacuo. Purification by column chromatography on silica gel (60 A, 70-230 mesh) doped with 10% of KF (hexanes/DCM 8:2) gave 0.096 g (53%) of 3fa as a colorless oil.
  • 53
  • [ 36854-57-6 ]
  • [ 370839-64-8 ]
  • [ 1448715-97-6 ]
YieldReaction ConditionsOperation in experiment
77% With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20℃; for 1h; General procedure: To a solution of pyridine-2-sulfonic acid benzylamide (234 mg, 1 mmol) in THF (10 mL) at 0C was added NaH (80 mg, 2 mmol, 60 % dispersion in mineral oil), followed by the appropriate acid chloride (1.2 mmol). The solution was stirred at room temperature for 1 hour and was then quenched with H2O (5 mL) and extracted with CH2Cl2 (2 x 10 mL), dried over sodium sulphate and filtered to give an oil. The crude material was purified by column chromatography (3:1 petrol/EtOAc) to give the acylated product.
  • 54
  • [ 578-66-5 ]
  • [ 36854-57-6 ]
  • [ 1111441-33-8 ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine; In dichloromethane; for 12h;Reflux; Inert atmosphere; General procedure: The corresponding carboxylic acid (1.5 mmol) was dissolved in SOCl2 (4 mmol) and stirred for 24 h at rt under nitrogen. After this period, the reaction mixture was concentrated in vacuum and diluted with anhydrous DCM (3 mL) under nitrogen. Then, the DCM solution of acid chloride was added to another RB flask containing the corresponding auxiliary (amine, 1 mmol) and Et3N (1.1 mmol) in anhydrous DCM (2 mL) at 0 C. Then, reaction mixture was stirred at rt for 10 min and then, the reaction mixture was refluxed for 12 h. After this period, the reaction mixture was diluted with DCM (5 mL) and washed with water followed by saturated aqueous NaHCO3 solution. The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuum and purification of the resulting reaction mixture by column chromatography (EtOAc/Hexanes=15:85) furnished the corresponding carboxamides (±)-1a-h, 1iB and 1j-(S).
  • 55
  • [ 504-29-0 ]
  • [ 36854-57-6 ]
  • (±)-2-phenyl-N-(pyridin-2-yl)butanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With triethylamine; In dichloromethane; for 12h;Reflux; Inert atmosphere; General procedure: The corresponding carboxylic acid (1.5 mmol) was dissolved in SOCl2 (4 mmol) and stirred for 24 h at rt under nitrogen. After this period, the reaction mixture was concentrated in vacuum and diluted with anhydrous DCM (3 mL) under nitrogen. Then, the DCM solution of acid chloride was added to another RB flask containing the corresponding auxiliary (amine, 1 mmol) and Et3N (1.1 mmol) in anhydrous DCM (2 mL) at 0 C. Then, reaction mixture was stirred at rt for 10 min and then, the reaction mixture was refluxed for 12 h. After this period, the reaction mixture was diluted with DCM (5 mL) and washed with water followed by saturated aqueous NaHCO3 solution. The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuum and purification of the resulting reaction mixture by column chromatography (EtOAc/Hexanes=15:85) furnished the corresponding carboxamides (±)-1a-h, 1iB and 1j-(S).
  • 56
  • [ 36854-57-6 ]
  • [ 2987-53-3 ]
  • (±)-N-(2-(methylthio)phenyl)-2-phenylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine; In dichloromethane; for 12h;Reflux; Inert atmosphere; General procedure: The corresponding carboxylic acid (1.5 mmol) was dissolved in SOCl2 (4 mmol) and stirred for 24 h at rt under nitrogen. After this period, the reaction mixture was concentrated in vacuum and diluted with anhydrous DCM (3 mL) under nitrogen. Then, the DCM solution of acid chloride was added to another RB flask containing the corresponding auxiliary (amine, 1 mmol) and Et3N (1.1 mmol) in anhydrous DCM (2 mL) at 0 C. Then, reaction mixture was stirred at rt for 10 min and then, the reaction mixture was refluxed for 12 h. After this period, the reaction mixture was diluted with DCM (5 mL) and washed with water followed by saturated aqueous NaHCO3 solution. The combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuum and purification of the resulting reaction mixture by column chromatography (EtOAc/Hexanes=15:85) furnished the corresponding carboxamides (±)-1a-h, 1iB and 1j-(S).
  • 57
  • [ 36854-57-6 ]
  • [ 88738-78-7 ]
  • [ 57585-10-1 ]
YieldReaction ConditionsOperation in experiment
100% General procedure: To a solution of methyl bis(2,2,2-trifluoroethyl)phosphonoacetate (1) (40 muL, 0.188 mmol) inanhydrous THF (1.9 mL) was added i-PrMgBr (0.77 mol/L in THF, 269 muL, 0.207 mmol), and thesolution was stirred at 0 C for 1 h under argon. After adding triethylamine (53 muL, 0.377 mmol)and 2-phenylpropionyl chloride (5a) (56 muL, 0.377 mmol), the mixture was stirred at 0 C for 1 hunder argon. The reaction mixture was treated with sat. NH4Cl aq (2 mL) and then extracted withCHCl3 (20 mL x 3). The extract was dried over anhydrous MgSO4, filtered, and concentrated invacuo. The oily residue was purified by silica gel column chromatography [n-hexane-AcOEt (12.5:1 to 11:1)] to afford allenyl ester 6a (34.7 mg, 98%).
  • 58
  • [ 36854-57-6 ]
  • diethyl {1-fluoro-2-[methoxy(methyl)amino]-2-oxoethyl}phosphonate [ No CAS ]
  • 2-fluoro-N-methoxy-N-methyl-4-phenylhexa-2,3-dienamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% General procedure: To a solution of diethyl {1-fluoro-2-[methoxy(methyl)amino]-2-oxoethyl}phosphonate (11) (40.0mg, 0.156 mmol) in anhydrous THF (1.6 mL) was added i-PrMgBr (0.74 mol/L in THF, 231 muL,0.171 mmol), and the solution was stirred at 0 C for 1 h under argon. After adding triethylamine(43 muL, 0.311 mmol) and 2-phenylpropionyl chloride (5a) (46 muL, 0.311 mmol), the mixture wasstirred at 0 C for 18 h under argon. The reaction mixture was treated with sat. NH4Cl aq (5 mL)and then extracted with CHCl3 (50 mL x 3). The extract was dried over anhydrous MgSO4, filtered,and concentrated in vacuo. The oily residue was purified by silica gel column chromatography[CHCl3-AcOEt (50:1)] to afford alpha-fluorinated allenyl carboxamide 14a (37.6 mg, 100%).
  • 59
  • [ 36854-57-6 ]
  • [ 1444335-07-2 ]
  • N-[5-(benzyloxy)-3,4,6-trimethylpyridin-2-yl]-2-phenylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine; In dichloromethane; at 20℃; for 5h; Example 7-20 Preparation of N-(5-benzyloxy-3,4,6-trimethylpyridine-2-yl)-2-phenylbutanamide (7t) 0.161 mL (1.155 mmol) of triethylamine and 0.169 mL (0.990 mmol) of <strong>[36854-57-6]2-phenylbutyryl chloride</strong> were sequentially added to 10 mL of CH2Cl2 containing 200 mg (0.825 mmol) of Compound 6, and then, the mixed solution was stirred at room temperature for 5 hours. The reaction solution was diluted with 100 mL of CH2Cl2, and then, washed with 10 mL of saturated sodium hydrogencarbonate aqueous solution twice and 10 mL of water twice. The CH2Cl2 solution was washed with saturated brine, dried with anhydrous MgSO4, filtered, and then, concentrated under reduced pressure. The residues were purified by column chromatography (EtOAC:Hex=1:3), thereby obtaining 248 mg (77%) of yellow taffy phase, i.e., Compound 7t. 1H-NMR (250 MHz, CHCl3-d) delta 7.90 (br s, 1H), 7.20-7.45 (m, 10H), 4.72 (s, 2H), 3.45 (t, J=7.4 Hz, 1H), 2.34 (s, 3H), 2.16-2.27 (m, 4H), 1.94 (s, 3H), 1.74-1.89 (m, 1H), 0.88 (t, J=7.3 Hz, 3H) ppm
77% With triethylamine; In dichloromethane; at 20℃; for 5h; 0.161 mL (1.155 mmol) of triethylamine and 0.169 mL (0.990 mmol) of <strong>[36854-57-6]2-phenylbutyryl chloride</strong> were sequentially added to 10 mL of CH2Cl2 containing 200 mg (0.825 mmol) of Compound 6, and then, the mixed solution was stirred at room temperature for 5 hours. The reaction solution was diluted with 100 mL of CH2Cl2, and then, washed with 10 mL of saturated sodium hydrogencarbonate aqueous solution twice and 10 mL of water twice. The CH2Cl2 solution was washed with saturated brine, dried with anhydrous MgSO4, filtered, and then, concentrated under reduced pressure. The residues were purified by column chromatography (EtOAC:Hex=1:3), thereby obtaining 248 mg (77%) of yellow taffy phase, i.e., Compound 7t.
  • 60
  • [ 36854-57-6 ]
  • [ 39900-63-5 ]
  • 2-cyano-4-methoxyphenyl 2-phenylbutanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-cyano-4-methoxyphenol With sodium hydride In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: 2-Phenylbutyryl chloride In tetrahydrofuran at 0 - 20℃;
  • 61
  • [ 36854-57-6 ]
  • [ 767-64-6 ]
  • N-(benzo[c][1,2,5]thiadiazol-4-yl)-2-phenylbutanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 2-Phenylbutyryl chloride; 4-Amino-2,1,3-benzothiadiazole With triethylamine Inert atmosphere; Stage #2: 2-Phenylbutyryl chloride In dichloromethane at 20℃; for 12h; Inert atmosphere;
  • 62
  • [ 36854-57-6 ]
  • [ 510-30-5 ]
  • (3,16-di-2-phenylbutanoyl)echinocystic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.29 g With triethylamine In dichloromethane at 20℃; for 24h; Cooling with ice; 8 Example 8 (3,16-b 2-phenyl-butyryl) echinocystic acid (compound 7) preparation of echinocystic acid 0.47g, soluble in 25mlCH 2 Cl 2 in, slowly dropping under ice bath 2-phenyl-butyrylchlorine 2 ml, then adding triethylamine 2 ml, stirring reaction under the normal temperature condition 24h, to be the reaction is complete, pressure reducing and recovering the solvent, drying, to obtain the crude product. The crude product is recrystallized with dichloromethane-petroleum ether, separation and purification with silica gel column (petroleum ether: ethyl acetate = 5:1), to obtain white powdery crystalline 0.29 g.
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