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Chemical Structure| 873-75-6
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Product Details of [ 873-75-6 ]

CAS No. :873-75-6 MDL No. :MFCD00004650
Formula : C7H7BrO Boiling Point : -
Linear Structure Formula :- InChI Key :VEDDBHYQWFOITD-UHFFFAOYSA-N
M.W : 187.03 Pubchem ID :70119
Synonyms :

Calculated chemistry of [ 873-75-6 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.27
TPSA : 20.23 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) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.03
Log Po/w (XLOGP3) : 1.15
Log Po/w (WLOGP) : 1.79
Log Po/w (MLOGP) : 2.3
Log Po/w (SILICOS-IT) : 2.37
Consensus Log Po/w : 1.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.15
Solubility : 1.32 mg/ml ; 0.00706 mol/l
Class : Soluble
Log S (Ali) : -1.17
Solubility : 12.7 mg/ml ; 0.0677 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.08
Solubility : 0.156 mg/ml ; 0.000832 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 873-75-6 ]

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

Application In Synthesis of [ 873-75-6 ]

* 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.

  • Upstream synthesis route of [ 873-75-6 ]
  • Downstream synthetic route of [ 873-75-6 ]

[ 873-75-6 ] Synthesis Path-Upstream   1~30

  • 1
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  • [ 132833-51-3 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 13, p. 6604 - 6614
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  • [ 132833-51-3 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 9, p. 2210 - 2213
  • 3
  • [ 136918-14-4 ]
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  • [ 153171-22-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2007, vol. 46, # 43, p. 8266 - 8269
  • 4
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  • [ 1670-14-0 ]
  • [ 23449-08-3 ]
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 24, p. 6723 - 6727
  • 5
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  • [ 589-17-3 ]
YieldReaction ConditionsOperation in experiment
98% With oxalyl dichloride In dichloromethane at 20℃; Reflux General procedure: To 16 (0.6 g, 0.6 mmol) was added dichloromethane (5 mL) in a round-bottom flask. After 10 min, oxalyl chlorideor oxalyl bromide was added (0.6 mmol). The reaction mixture was magnetically stirred at room temperature. Uponcessation of gas evolution, 4 was added (0.5 mmol), and the reaction mixture was heated to reflux. After thereaction was complete according to TLC analysis, the mixture was cooled to room temperature and filtered. Thesolid on the funnel was washed with dichloromethane (3 × 10 mL), and the filtrate was concentrated under reducedpressure to afford the desired product 5 in an essentially pure state based on 1H and 13C NMR spectroscopicanalyses.
81.6% With dmap; thionyl chloride In dichloromethane at 20℃; for 0.166667 h; Cooling with ice [0193] To a solution of (4-bromo-phenyl)-methanol (19.0 g, 0.1015 mol) in dichloromethane (190 mL) was added thionyl chloride (18.89 mL 0.2539 mol) slowly at ice temperature and catalytic DMAP. Resulting reaction mass was stirred at room temperature for 10 minutes. Reaction mass was concentrated, diluted with ethyl acetate (500 mL) and washed with sodium bicarbonate solution (200 mL) , Organic layer was washed with water (2 x 200 mL) , dried over anhydrous sodium sulphate and filtered . Volatiles were concentrated under reduced pressure to obtain the product as pale yellow liquid (17.0 g, 81.6 percent).
80% With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane for 1.08333 h; Thionyl chloride (121 J..LL, 1.67 mmol) was added to benzotriazole (239 mg, 2.0 mmol).The resulting solution was dissolved in CHzClz (5 mL). After 5 min, this solution wasadded slowly to the solution of the alcohol 9a in CHzClz (10 mL). The benzotriazole saltstarted to precipitate. After 1h of reaction, the salt was filtered. The organic phase waswashed by water and NaOH solution (0.5 M). The organic phase was dried over MgS04and the solvent was removed under reduced pressure to give the desired chlorinatedcompound as a yellow oil (m = 220 mg, 80 percent). 1H NMR (300 MHz, CDCh): 8 (ppm) 4.91(dd, J = 12.0, 30.8 Hz, 2H), 7.18 (d, J = 8.0 Hz, 2H), 7.49 (d, J = 7.9 Hz, 2H).
Reference: [1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1397 - 1405
[2] Organic Letters, 2013, vol. 15, # 1, p. 108 - 111
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 24, p. 4016 - 4024
[4] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 11, p. 3434 - 3436
[5] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064
[6] Patent: WO2015/95821, 2015, A1, . Location in patent: Paragraph 0193
[7] Patent: WO2017/134188, 2017, A1, . Location in patent: Page/Page column 61
[8] Molecules, 2011, vol. 16, # 7, p. 5665 - 5673
[9] Journal of the Chemical Society, 1935, p. 1815,1818
[10] Journal of the American Chemical Society, 1951, vol. 73, p. 2813,2818
[11] Gazzetta Chimica Italiana, 1888, vol. 18, p. 239
[12] Canadian Journal of Chemistry, 1983, vol. 61, p. 1472 - 1480
[13] Tetrahedron Letters, 2014, vol. 55, # 19, p. 3045 - 3048
[14] Chemical Communications, 2017, vol. 53, # 54, p. 7545 - 7548
  • 6
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  • [ 1609172-81-7 ]
  • [ 589-17-3 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 19, p. 3045 - 3048
  • 7
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  • [ 1074-61-9 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 26, p. 9681 - 9686
  • 8
  • [ 2554-06-5 ]
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  • [ 1074-61-9 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 1, p. 63 - 66
  • 9
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  • [ 75-65-0 ]
  • [ 59247-47-1 ]
YieldReaction ConditionsOperation in experiment
87% With 1H-imidazole; tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water at 80℃; for 7 h; Green chemistry General procedure: To a mixture of benzyl alcohol (108 mg, 1.0 mmol) and TBHP(180 mg, 2.0 mmol) in water (3 ml), the catalyst TBAI (73.8 mg,0.2 mmol), imidazole (136 mg, 2.0 mmol), and MeOH (2 ml)were added, and the mixture was stirred at 80 °C for 8 h. Theprogress of the reaction was monitored by TLC. After completionof reaction, the reaction mixture was cooled to room temperature.Then MeOH was distilled out, and the organic productwas extracted with ethyl acetate (3 × 10 ml), repeatedly washedwith distilled water (4 × 5 ml) to remove the unreacted TBHP,dried with anhydrous sodium sulfate, and the solvent was evaporatedunder reduced pressure to afford methyl benzoate (112mg, yield 82percent).
Reference: [1] Synlett, 2018, vol. 29, # 16, p. 2208 - 2212
  • 10
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  • [ 143-33-9 ]
  • [ 874-89-5 ]
Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 10, p. 2890 - 2891
  • 11
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  • [ 874-89-5 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 2, p. 202 - 205
  • 12
  • [ 1071-46-1 ]
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  • [ 40640-98-0 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 52, p. 7413 - 7415
  • 13
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  • [ 89343-06-6 ]
  • [ 10602-04-7 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; tri-tert-butyl phosphine; triethylamine In tetrahydrofuran at 70℃;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 3 h;
General procedure: 4.1.4.1. General procedure for the coupling of a terminal alkynewith an aryl halide using a palladium-catalyzed cross-coupling (Sonogashira)protocol. To an oven-dried round-bottom flask or screwcap tube equipped with a magnetic stir bar were added the arylhalide, the terminal alkyne, PdCl2(PPh3)2 or PdCl2(PhCN)2 (w2 molpercent per aryl halide), CuI (w4 mol percent per aryl halide), and in the case ofusing PdCl2(PhCN)2, alsow4 mol percent per aryl halide of HP(tert-Bu)3. Asolvent system of TEA and/or THF was added depending on thesubstrates. Upon completion, the reaction was quenched witha saturated solution of NH4Cl. The organic layer was then dilutedwith diethyl ether or CH2Cl2, and washed with water or saturatedNH4Cl (1). The combined aqueous layers were extracted withhexanes, diethyl ether, or CH2Cl2 (2). The combined organic layerswere dried over MgSO4 and filtered, and the solvent was removedfrom the filtrate in vacuo to afford the crude product, which waspurified by column chromatography (silica gel). Eluents and otherslight modifications are described below for each compound.4.1.4.2. General procedure for deprotection of TIPS-protected alkynesusing TBAF. In a round-bottomed flask equipped witha magnetic stir bar, the protected alkyne was dissolved in THF([protected alkyne]0.05e0.1 M). TBAF in THF (1.0 M, 1.1 equiv peralkyne) was added. The mixture was stirred at rt for 0.5 h or untilthe reaction was complete (monitored by TLC). The reaction wasquenched with a saturated solution of NH4Cl. The organic layer wasthen diluted with ethyl acetate. The organic layer was dried overMgSO4 and filtered, and the solvent was removed from the filtratein vacuo to afford the crude product, which was purified by columnchromatography (silica gel).
Reference: [1] Tetrahedron, 2015, vol. 71, # 35, p. 5965 - 5972
  • 14
  • [ 873-75-6 ]
  • [ 10602-04-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2004, vol. 43, # 29, p. 3814 - 3818
[2] Chemistry - A European Journal, 2013, vol. 19, # 29, p. 9452 - 9456
[3] Patent: US2013/266644, 2013, A1,
[4] Synthesis (Germany), 2014, vol. 46, # 3, p. 348 - 356
[5] Patent: CN105622638, 2016, A,
[6] Patent: US9758545, 2017, B2,
[7] Patent: WO2018/14802, 2018, A1,
  • 15
  • [ 79-24-3 ]
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  • [ 131981-75-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 13, p. 1975 - 1978
  • 16
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  • [ 122-52-1 ]
  • [ 38186-51-5 ]
YieldReaction ConditionsOperation in experiment
90% at 120℃; for 24 h; Inert atmosphere To a 20 mL tubular reactor was added 4-bromobenzyl alcohol (93.0 mg, 0.50 mmol)(3.8 mg, 0.01 mmol, 2 molpercent), protected by vacuum nitrogen and then heated to 120 ° C under solvent-free conditions 24h After the TLC monitoring reaction was complete, the product was purified by column chromatography and the yield was 90percent.
Reference: [1] Patent: CN106543221, 2017, A, . Location in patent: Paragraph 0030; 0031; 0032; 0033
[2] Green Chemistry, 2018, vol. 20, # 15, p. 3408 - 3413
  • 17
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  • [ 80936-82-9 ]
Reference: [1] Patent: WO2015/66413, 2015, A1,
  • 18
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  • [ 53531-69-4 ]
Reference: [1] Patent: US2014/163024, 2014, A1,
[2] Patent: US2014/163110, 2014, A1,
[3] Patent: WO2015/177325, 2015, A1,
  • 19
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  • [ 59016-93-2 ]
Reference: [1] Tetrahedron Asymmetry, 2003, vol. 14, # 22, p. 3435 - 3446
[2] European Journal of Organic Chemistry, 2000, # 23, p. 3825 - 3834
  • 20
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  • [ 108-98-5 ]
  • [ 6317-56-2 ]
Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 4, p. 1664 - 1672
  • 21
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  • [ 107834-03-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 13, p. 2390 - 2410
  • 22
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  • [ 63697-96-1 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 29, p. 9452 - 9456
  • 23
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  • [ 86718-08-3 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 10, p. 1631 - 1636
[2] Synthesis, 2010, # 9, p. 1505 - 1511
[3] Green Chemistry, 2012, vol. 14, # 5, p. 1268 - 1271
  • 24
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YieldReaction ConditionsOperation in experiment
66% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tri-tert-butyl phosphine In triethylamine at 130℃; for 4 h; Inert atmosphere; Microwave irradiation To a solution of (4-bromophenyl) methanol (935mg, 5mmol) in dry TEA was added Pd (PPh3) 2Cl2 (175mg, 0.25mmol) , CuI (48mg, 0.25mmol) and P (t-Bu) 3 (51mg, 0.25mmol) under N2 atmosphere. The reaction mixture was stirred for 5mins, followed by addition of ethynyltrimethylsilane (980mg, 10mmol) dropwise. The reaction mixture was then microwaved at 130 for 4hrs. The reaction mixture was cooled to room temperature, filtered over celite. Solvents were removed from the filtrate in vacuo, then the residue was extracted by EtOAc/H2O 3 times. The organic layer was combined, washed with brine, dried over Na2SO4 and further pufrified by silica gel column chromatography (PE/EA4/1) to give 670mg of (4- ( (trimethylsilyl) ethynyl) phenyl) methanol as a brown oil (66) .[0633]To a solution of (4- ( (trimethylsilyl) ethynyl) phenyl) methanol (250mg, 1.23mmol) in THF was added TBAF (500mg, 2.45mmol) in portions at 0. The reaction mixture was stirred at 0 to room temperature for 3hrs. Solvents were removed from the mixture in vacuo, and the residue was extracted by EtOAc/H2O 3 times. The organic layer was combined, washed with brine, dried over Na2SO4 and further pufrified by silica gel column chromatography (PE/EA4/1) to give 170mg of (4-ethynylphenyl) methanol as a brown oil (100) . 1H NMR (400Hz, CDCl3) δ7.45-7.49 (m, 2H) , 7.21-7.26 (m, 2H) , 4.69 (s, 1H) , 4.65 (s, 2H) .
1.274 g With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine; triphenylphosphine In N,N-dimethyl-formamideMicrowave irradiation; Heating; Inert atmosphere A solution of 4-Bromobenzyl alcohol (1.276 g, 6.82 mmol), Ethynyltrimethylsilane (1.061 ml, 7.51 mmol), PdCl2(PPh3)2 (24 mg, 0.034 mmol), Copper iodide (52 mg, 0.273 mmol), Triphenylphosphine (358 mg, 1.365 mmol), Diethylamine (10.70 ml, 102 mmol) in 2 ml of dry DMF (dimethylformamide) was heated under argon in a microwave oven at 150° C. for 30 min. The mixture was filtered. The filtrate was acidified with 1 M HCl and extracted 3 times with ether. The combined organic layers were washed with bicarbonate and water, dried over MgSO4 and concentrated to afford 3 (1.274 g, 6.23 mmol, 91percent yield) as a brown solid.
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 50, p. 12190 - 12197
[2] Synthesis (Germany), 2014, vol. 46, # 3, p. 348 - 356
[3] Angewandte Chemie - International Edition, 2004, vol. 43, # 29, p. 3814 - 3818
[4] Patent: WO2018/14802, 2018, A1, . Location in patent: Paragraph 0364
[5] Chemistry - A European Journal, 2013, vol. 19, # 29, p. 9452 - 9456
[6] Chemistry - An Asian Journal, 2011, vol. 6, # 10, p. 2816 - 2824
[7] Patent: CN105622638, 2016, A, . Location in patent: Paragraph 0328
[8] Patent: US9758545, 2017, B2, . Location in patent: Page/Page column 19; 20; 26
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  • [ 1066-54-2 ]
  • [ 275386-60-2 ]
Reference: [1] Patent: US2013/266644, 2013, A1, . Location in patent: Page/Page column
  • 26
  • [ 873-75-6 ]
  • [ 99768-12-4 ]
  • [ 393522-78-6 ]
YieldReaction ConditionsOperation in experiment
24% With palladium diacetate; sodium carbonate In water; N,N-dimethyl-formamide at 70℃; To a solution of (4-bromophenyl)methanol (500 mg, 2.94 mmol) and [4-(methoxycarbonyl) phenyl]boronic acid (550 mg, 3.53 mmol) in DMF (20 mL) was added Pd(OAc)2 (200 mg, 735 μmol) and Na2CO3 (3 g in 20 mL H2O).
The reaction mixture was allowed to stir at 70 °C.
After 48 h, an extraction with EtOAc was performed; the organic layers were combined and washed with brine, dried over MgSO4, filtrated and concentrated in vacuo.
Column chromatography (EtOAc/Hept 1:4) yielded the product (170 mg, 24percent) as white crystals. RF = 0.3 (EtOAc/Hept 1:1).
1H NMR (400 MHz, CDCl3) δ 8.15-8.06 (m, 2H), 7.70-7.58 (m, 4H), 7.52-7.43 (m, 2H), 4.77 (d, J = 3.1 Hz, 2H), 4.07-3.67 (m, 3H), 1.75 (br s, 1H, OH) ppm. FTIR = 3305, 3032, 1718, 1604, 1432, 1399, 1286, 1271, 1220, 1111, 765 cm-1. HRMS (EI) calcd for C15H14O3 (M)+ 242.0942, found 242.0919.
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 20, p. 5593 - 5603
  • 27
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  • [ 73183-34-3 ]
  • [ 302348-51-2 ]
YieldReaction ConditionsOperation in experiment
90% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 85℃; Inert atmosphere p-Bromobenzyl alcohol (Compound 1, 1.0 g, 5.35 mmol) was dissolved in 10 mL of dry 1,4-dioxane solution, and boranoic acid pinacol ester (247 mg, 5.88 mmol), potassium acetate and pdCl 2 ( Dppf), under N2 protection, heat to 85 ° C to stir the reaction. After the reaction was completed by thin layer chromatography, the solvent was evaporated under reduced pressure, and ethyl acetate (200 ml) was added and thenThe organic phase was dried over anhydrous sodium sulfate and concentrated under reduced vacuo.The crude product was purified by column chromatography (mobile phase ethyl acetate: petroleum ether = 1:8-1:4)Obtained 181 mg of a pale yellow oily liquid with a yield of 90percent.
1500 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 90℃; for 16 h; A mixture of (4-bromophenyl)methanol (1 g, 5.35 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (4.07 g, 16.04 mmol), KOAc (1.05 g, 10.69 mmol) and Pd(dppf)Cl2.CH2Cl2 (873.27 mg, 1.07 mmol) in 1,4-Dioxane (20 mL) was stirred at 90 C for 16 hours. After cooling to r.t., the mixture was concentrated to give the crude product. The crude product was purified by flash chromatography on silica gel (EtOAc in PE = 0 to 50percent) to give the product (1500 mg) as oil. H NMR (400MHz DMSO-d6) __ = 7.63 (d, 2H), 7.32 (d, 2H), 5.23 (t, 1H), 4.51 (d, 2H), 1.29 (s, 12H).
Reference: [1] Patent: CN108148098, 2018, A, . Location in patent: Paragraph 0058; 0059; 0060
[2] Journal of the American Chemical Society, 2018, vol. 140, # 19, p. 6109 - 6121
[3] Patent: US2012/184520, 2012, A1, . Location in patent: Page/Page column 17
[4] Patent: CN107445885, 2017, A, . Location in patent: Paragraph 0177; 0180
[5] Patent: WO2018/98499, 2018, A1, . Location in patent: Page/Page column 215
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Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1463 - 1467
[2] Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1463 - 1467
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Reference: [1] Organic Letters, 2017, vol. 19, # 11, p. 2809 - 2812
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  • [ 916766-83-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 7, p. 2875 - 2894
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