65020-70-4|4-(4-Fluorophenyl)-1H-imidazole| Ambeed

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+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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1
Citronellyl mesylate [ No CAS ]
[ 65020-70-4 ]
[ 95086-76-3 ]

Yield	Reaction Conditions	Operation in experiment
2%	With sodium hydride In N,N-dimethyl-formamide

Reference： [1]Kuwano, Eiichi; Takeya, Ryuko; Eto, Morifusa [Agricultural and Biological Chemistry, 1984, vol. 48, # 12, p. 3115 - 3120]

Yield	Reaction Conditions	Operation in experiment
	4-Fluor-phenacylbromid, Formamid;

3
[ 60100-09-6 ]
[ 403-29-2 ]
[ 65020-70-4 ]

Yield	Reaction Conditions	Operation in experiment
51%	at 170 - 180℃; Inert atmosphere;
45%	Stage #1: formamide; 2-bromo-4'-fluoroacetophenone In water at 140℃; for 4h; Stage #2: With sodium hydroxide In water	1 In a 50 ml pear flask 2-bromo-1-(4-fluorophenyl)ethanone (5.93 g, 27.31 mmol), formamide (13.45 ml, 339 mmol) and water (1 ml) were placed. The reaction was heated at 140° C. for 4 hours. Then it was cooled to room temperature and poured into 150 ml of water. The precipitate was filtered off, washed with water. The filtrate's pH was set to 12 by adding 10% NaOH solution. The resultant precipitate was filtered off, washed with water and dried under vacuum. (Yield: 2.02 g, 45%).
43%	at 170℃; for 4h; Inert atmosphere;

Heating;

Reference： [1]Location in patent: experimental part Kumar, Sanjeev; Jaller, Daniel; Patel, Bhumika; LaLonde, Judith M.; DuHadaway, James B.; Malachowski, William P.; Prendergast, George C.; Muller, Alexander J. [Journal of Medicinal Chemistry, 2008, vol. 51, # 16, p. 4968 - 4977]
[2]Current Patent Assignee: Bial - Sgps, S.A - US2012/65191, 2012, A1 Location in patent: Page/Page column 28
[3]Location in patent: experimental part Xiao, Hai-Yun; Wu, Dauh-Rurng; Malley, Mary F.; Gougoutas, Jack Z.; Habte, Sium F.; Cunningham, Mark D.; Somerville, John E.; Dodd, John H.; Barrish, Joel C.; Nadler, Steven G.; Dhar, T. G. Murali [Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 1270 - 1280]
[4]Ho, Koc-Kan; Auld, Douglas S.; Bohnstedt, Adolph C.; Conti, Paolo; Dokter, Wim; Erickson, Shawn; Feng, Daming; Inglese, Jim; Kingsbury, Celia; Kultgen, Steven G.; Liu, Rong-Qiang; Masterson, Christopher M.; Ohlmeyer, Michael; Rong, Yajing; Rooseboom, Martijn; Roughton, Andrew; Samama, Philippe; Smit, Martin-Jan; Son, Ellen; van der Louw, Jaap; Vogel, Gerard; Webb, Maria; Wijkmans, Jac; You, Ming [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 10, p. 2724 - 2728]

4
[ 115419-76-6 ]
[ 65020-70-4 ]
4-butyl-6-chloro-2-[4-(4-fluoro-phenyl)-imidazol-1-yl]-pyrimidine [ No CAS ]
4-butyl-2-chloro-6-[4-(4-fluoro-phenyl)-imidazol-1-yl]-pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide

Reference： [1]Ho, Koc-Kan; Auld, Douglas S.; Bohnstedt, Adolph C.; Conti, Paolo; Dokter, Wim; Erickson, Shawn; Feng, Daming; Inglese, Jim; Kingsbury, Celia; Kultgen, Steven G.; Liu, Rong-Qiang; Masterson, Christopher M.; Ohlmeyer, Michael; Rong, Yajing; Rooseboom, Martijn; Roughton, Andrew; Samama, Philippe; Smit, Martin-Jan; Son, Ellen; van der Louw, Jaap; Vogel, Gerard; Webb, Maria; Wijkmans, Jac; You, Ming [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 10, p. 2724 - 2728]

5
[ 65020-70-4 ]
(S)-2-{6-Butyl-2-[4-(4-fluoro-phenyl)-imidazol-1-yl]-pyrimidin-4-ylamino}-4-methyl-pentanoic acid (3-ethoxy-propyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: DBU / dimethylformamide 2: DIEA / dimethylsulfoxide / 80 °C

Reference： [1]Ho, Koc-Kan; Auld, Douglas S.; Bohnstedt, Adolph C.; Conti, Paolo; Dokter, Wim; Erickson, Shawn; Feng, Daming; Inglese, Jim; Kingsbury, Celia; Kultgen, Steven G.; Liu, Rong-Qiang; Masterson, Christopher M.; Ohlmeyer, Michael; Rong, Yajing; Rooseboom, Martijn; Roughton, Andrew; Samama, Philippe; Smit, Martin-Jan; Son, Ellen; van der Louw, Jaap; Vogel, Gerard; Webb, Maria; Wijkmans, Jac; You, Ming [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 10, p. 2724 - 2728]

6
[ 111409-79-1 ]
[ 65020-70-4 ]
[ 1046136-24-6 ]
[ 1046136-19-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 72% 2: 7%	With copper(l) iodide; caesium carbonate In 1,4-dioxane for 18h; Heating;
	With copper(l) iodide; 2-acetylcyclohexanone In 1,4-dioxane at 50℃; Reflux; Inert atmosphere; regioselective reaction;

Reference： [1]Laroche, Christophe; Li, Jing; Freyer, Matthew W.; Kerwin, Sean M. [Journal of Organic Chemistry, 2008, vol. 73, # 16, p. 6462 - 6465]
[2]Location in patent: scheme or table Li, Jing; Kaoud, Tamer S.; Laroche, Christophe; Dalby, Kevin N.; Kerwin, Sean M. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 22, p. 6293 - 6297]

7
[ 791602-99-8 ]
[ 65020-70-4 ]
[ 926659-96-3 ]
C₂₉H₃₁FN₂OSi [ No CAS ]
C₂₈H₂₉FN₂OSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium phosphate; [Ir(cod)(κ2-(Ra,Rc,Rc)-(C10H6)2O2PN(CHCH2(2-MeOC6H)4)2H(ethylene)] In tetrahydrofuran at 20℃; for 22h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

Reference： [1]Stanley, Levi M.; Hartwig, John F. [Journal of the American Chemical Society, 2009, vol. 131, # 25, p. 8971 - 8983]

8
[ 50-00-0 ]
[ 65020-70-4 ]
[ 1150847-15-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With water In ethanol at 20℃; for 1h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Xiao, Hai-Yun; Wu, Dauh-Rurng; Malley, Mary F.; Gougoutas, Jack Z.; Habte, Sium F.; Cunningham, Mark D.; Somerville, John E.; Dodd, John H.; Barrish, Joel C.; Nadler, Steven G.; Dhar, T. G. Murali [Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 1270 - 1280]

9
[ 49844-90-8 ]
[ 65020-70-4 ]
[ 1244039-76-6 ]

Yield	Reaction Conditions	Operation in experiment
77.9%	Stage #1: 4-(4-fluorophenyl)-1H-imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Stage #2: 4-Chloro-2-methylthiopyrimidine In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	3.1 To solution of 40C to ambient temperature, then quenched by addition of water (1 ml). The quenched mixture was concentrated and residue was partitioned between CH2Cl2/] hO (60 ml/30 ml). CH2CI2 layer was collected, washed with brine (30 ml), concentrated and the solid residue was mixed with BOAc (10 ml), and filtered to yield a solid, The filter cake was rinsed with M TBE (20 ml) to yield 13A as a solid (2.B g, 7,79 nunol, yield 77.9%). LCMS (wt&;): 287.2

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2010/100127, 2010, A1 Location in patent: Page/Page column 57

10
[ 144-55-8 ]
[ 403-29-2 ]
[ 65020-70-4 ]

Yield	Reaction Conditions	Operation in experiment
	With formamide In ethyl acetate	1.a (S)-1-((5aR,6S)-1-(4-Fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinolin-6-yl)-1-(thiophen-2-yl)ethanol (a) A mixture of 2-bromo-1-(4-fluorophenyl)ethanone (10.9 g, 50 mmol) and formamide (14 mL, 350 mmol) was stirred at 170° C. under nitrogen for 4 hr. The reaction mixture was cooled and mixed with ethyl acetate (40 mL). Saturated aqueous sodium bicarbonate solution (50 mL) was added with caution while the mixture was cooled in an ice-water bath. The aqueous layer was separated and extracted with ethyl acetate (2*40 mL). The combined organic solutions were washed with water (30 mL) and brine (30 mL), dried (Na2SO4), and concentrated. Silica gel flash chromatography (10-100% ethyl acetate in hexanes) gave 4-(4-fluorophenyl)-1H-imidazole (3.46 g, 21 mmol, 43% yield) as a solid. MS found: (M+H)+=163.1.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2011/263494, 2011, A1

11
[ 65020-70-4 ]
[ 1150847-15-6 ]

Yield	Reaction Conditions	Operation in experiment
	With formaldehyd In ethanol; water	1.b (S)-1-((5aR,6S)-1-(4-Fluorophenyl)-5a-methyl-5,5a,6,7,8,9-hexahydroimidazo[1,5-b]isoquinolin-6-yl)-1-(thiophen-2-yl)ethanol (b) To a stirred solution of 4-(4-fluorophenyl)-1H-imidazole (10 g, 62 mmol) in 95% ethanol (25 mL) was added aqueous formaldehyde solution (37%, 9 mL) slowly. The reaction mixture was stirred at RT for 1 hr before water (25 mL) was added. The reaction mixture was stirred at RT for an additional 3 hr. The solid that separated from solution out was filtered, washed with aqueous ethanol solution, and dried to give (4-(4-fluorophenyl)-1H-imidazol-1-yl)methanol (11.4 g, 59 mmol, 96% yield) as a solid. MS found: (M+H-CH2O)+=163.1.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2011/263494, 2011, A1

12
[ 141699-59-4 ]
[ 65020-70-4 ]
[ 1615729-70-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 4-(4-fluorophenyl)-1H-imidazole With sodium hydride In 1-methyl-pyrrolidin-2-one; mineral oil at 20℃; for 0.75h; Stage #2: 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate In 1-methyl-pyrrolidin-2-one; mineral oil at 80℃; for 16.33h;	Intermediate 3A: teri-butyl 4-(4-(4-fluorophenyl)-lH-imidazol-l-yl)piperidine-l- carboxylate Intermediate 3A was synthesized according to the procedure described in PCT Publication No. WO 2010/091409 (PCT/US2010/023637). To a solution of 4-(4- fiuorophenyl)-lH-imidazole (10.0 g, 61.7 mmol) in NMP (154 mL) was added NaH (60% suspension in mineral oil, 10.61 g, 265 mmol) and the reaction mixture was stirred at rt for 45 min. To this was added, dropwise over 20 min., a solution of Intermediate 2 (79 g, 284 mmol) in NMP (150 mL). The resultant mixture was heated in an oil-bath at 80 °C for 16 h. It was then cooled to rt, diluted with ~1 L water and extracted with EtOAc (4x200 mL). The combined organics were washed with water (5x100 mL) and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and purified by silica gel chromatography (300 g Thomson BIOTAGE column, eluting with 5% EtOAc in CH2Cl2to isolate unreacted Intermediate 2, and then 5% MeOH in CH2C12) to provide the desired Intermediate 3A (19.5 g, 92% yield) as a buff solid. HPLC Ret. Time: 3.06 min. (Method A). MS(ES): m/z= 346.14 [M+H]+. 1H NMR (400MHz, chloroform-d) δ ppm 8.02 (s, 1H), 7.83 - 7.72 (m, 2H), 7.23 (d, J= .5 Hz, 1H), 7.15 - 7.04 (m, 2H), 4.44 - 4.20 (m, 3H), 3.93 - 3.80 (m, 1H), 3.03 (ddd, J=13.4, 9.9, 3.3 Hz, 1H), 2.96 - 2.80 (m, 2H), 2.15 (d, J=12.3 Hz, 2H), 1.89 (qd, J=12.4, 4.3 Hz, 2H), 1.55 - 1.48 (m, 9H).

Reference： [1]Current Patent Assignee: BIOCON LIMITED; BRISTOL-MYERS SQUIBB CO - WO2014/100533, 2014, A1 Location in patent: Page/Page column 69

13
[ 3240-94-6 ]
[ 65020-70-4 ]
[ 1615729-91-3 ]

Yield	Reaction Conditions	Operation in experiment
51.9%	With methyllithium; dimethyl sulfoxide at 20 - 80℃; for 16.67h; Inert atmosphere;	Intermediate 7A: 4-(2-(4-(4-fluorophenyl)-lH-imidazol-l-yl)ethyl)morpholine Intermediate 7A was synthesized according to the procedure described in PCT Publication No. WO 2009/152825 (PCT/DK2009/050134). A 250 mL round-bottom flask was charged under nitrogen with DMSO (83 mL, 1172 mmol). To it was added methyllithium (8.48 mL, 13.57 mmol) in a dropwise manner. This mixture was stirred at rt for 40 min. so as to generate dimsyl anion. Simultaneously, in another round-bottom flask was prepared a solution of 4-(4-fluorophenyl)-lH-imidazole (2.0 g, 12.33 mmol) and 4-(2-chloroethyl)morpholine (2.214 g, 14.80 mmol) in DMSO (24.67 mL). The latter solution was added dropwise to the generated dimsyl anion at rt. The resultant reaction mixture was heated at 80 °C for 16 h. It was then cooled to rt, diluted with ~1 L water and extracted with EtOAc (3x150 mL). The combined organics were washed with water (5x100 mL) and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and purified by silica gel chromatography (240 g Thomson BIOTAGE column, eluting with 20% EtOAc in CH2C12 to isolate unreacted 4-(4-fiuorophenyl)-lH-imidazole, and then with 100% EtOAc) to provide Intermediate 7A (1.763 g, 51.9% yield) as a brown solid. HPLC Ret. Time 1.48 min. (Method A). MS(ES): m/z= 276.16 [M+H]+. 1H NMR (400MHz, chloroform-d) δ ppm 7.87 (s, 1H), 7.81 - 7.72 (m, 2H), 7.33 - 7.23 (m, 1H), 7.15 - 7.03 (m, 2H), 4.15 (t, J=6.3 Hz, 2H), 3.80 - 3.69 (m, 4H), 2.79 (t, J=6.1 Hz, 2H), 2.60 - 2.49 (m, 4H).

Reference： [1]Current Patent Assignee: BIOCON LIMITED; BRISTOL-MYERS SQUIBB CO - WO2014/100533, 2014, A1 Location in patent: Page/Page column 77; 78

14
[ 3188-13-4 ]
[ 65020-70-4 ]
4-(4-fluorophenyl)-1-(ethoxymethyl)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 3h;

Reference： [1]Albertshofer, Klaus; Mani, Neelakandha S. [Journal of Organic Chemistry, 2016, vol. 81, # 3, p. 1269 - 1276]

15
[ 65020-70-4 ]
2-chloro-1-(ethoxymethyl)-4-(4-fluorophenyl)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 3 h / 20 °C 2.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran; toluene / 0.5 h / 0 °C 2.2: -25 °C

Reference： [1]Albertshofer, Klaus; Mani, Neelakandha S. [Journal of Organic Chemistry, 2016, vol. 81, # 3, p. 1269 - 1276]

16
[ 65020-70-4 ]
2-chloro-1-(ethoxymethyl)-5-fluoro-4-(4-fluorophenyl)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 3 h / 20 °C 2.1: 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex / tetrahydrofuran; toluene / 0.5 h / 0 °C 2.2: -25 °C 3.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran / 0.17 h / -78 - -70 °C / Inert atmosphere; Schlenk technique 3.2: 0.08 h / -78 °C / Inert atmosphere; Schlenk technique

Reference： [1]Albertshofer, Klaus; Mani, Neelakandha S. [Journal of Organic Chemistry, 2016, vol. 81, # 3, p. 1269 - 1276]

17
[ 75-03-6 ]
[ 65020-70-4 ]
1,3-diethyl-(4-(4‘-fluorphenyl)-1H-imidazol-2-ium) iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate In acetonitrile at 110℃; for 672h; Reflux;
	With potassium carbonate In acetonitrile at 82℃; Microwave irradiation;	2.2. General synthesis of the phenylimidazolium halides ( 2a-2h ) General procedure: An amount of 0.20 g of the respective phenylimidazole 1a - 1d and 1.0 equivalent of K 2 CO 3 were added to 2.0 mL of acetonitrile, 3 equivalents of ethyl iodiode (for 2a -2d ) or 2-bromopropane (for 2e -2h ), respectively, were added, and the mixture was reacted for 8-54 h in a microwave at 82 °C, 50 W and 10 psi. The progress of the reaction was monitored by thin layer chromatography. The liquid phase was removed, the solid phase washed with methanol, and the volume of the combined liquid phases was reduced us- ing a rotary evaporator. Further work-up for 2a -2d : The residue was dissolved in dichloromethane and filtered using a syringe filter (0.2 μM) to remove the remaining K 2 CO 3 . Dichloromethane was re- moved by evaporation under reduced pressure resulting in an oily residue with some precipitate. A small amount of acetonitrile was added for dissolution and the product was precipitated with 10 mL of 1/1 ethylacetate/ n -hexane (V/V) and repeatedly cooled for 24 h at -25 °C until no further precipitate was obtained. The combined precipitates were dried using a rotary evaporator followed by dry- ing under reduced pressure at 40 °C for a period of 3 days. Further work-up for 2e -2h : The products were purified by column chro- matography over silica with ethylacetate/ n -hexane/methanol mix- tures (8/2/0 → 8/2/1 → 8/2/10) as eluent. The volume of the com- bined eluates was reduced with a rotary evaporator, filtered using a syringe filter (0.2 μm), and dried under reduced pressure at 40 °C for 3 days.
	With potassium carbonate In acetonitrile at 82℃; Microwave irradiation;	2.2. General synthesis of the phenylimidazolium halides ( 2a-2h ) General procedure: An amount of 0.20 g of the respective phenylimidazole 1a - 1d and 1.0 equivalent of K 2 CO 3 were added to 2.0 mL of acetonitrile, 3 equivalents of ethyl iodiode (for 2a -2d ) or 2-bromopropane (for 2e -2h ), respectively, were added, and the mixture was reacted for 8-54 h in a microwave at 82 °C, 50 W and 10 psi. The progress of the reaction was monitored by thin layer chromatography. The liquid phase was removed, the solid phase washed with methanol, and the volume of the combined liquid phases was reduced us- ing a rotary evaporator. Further work-up for 2a -2d : The residue was dissolved in dichloromethane and filtered using a syringe filter (0.2 μM) to remove the remaining K 2 CO 3 . Dichloromethane was re- moved by evaporation under reduced pressure resulting in an oily residue with some precipitate. A small amount of acetonitrile was added for dissolution and the product was precipitated with 10 mL of 1/1 ethylacetate/ n -hexane (V/V) and repeatedly cooled for 24 h at -25 °C until no further precipitate was obtained. The combined precipitates were dried using a rotary evaporator followed by dry- ing under reduced pressure at 40 °C for a period of 3 days. Further work-up for 2e -2h : The products were purified by column chro- matography over silica with ethylacetate/ n -hexane/methanol mix- tures (8/2/0 → 8/2/1 → 8/2/10) as eluent. The volume of the com- bined eluates was reduced with a rotary evaporator, filtered using a syringe filter (0.2 μm), and dried under reduced pressure at 40 °C for 3 days.

Reference： [1]Schmidt, Claudia; Karge, Bianka; Misgeld, Rainer; Prokop, Aram; Franke, Raimo; Brönstrup, Mark; Ott, Ingo [Chemistry - A European Journal, 2017, vol. 23, # 8, p. 1869 - 1880]
[2]Schmidt, Janina; Wölker, Jessica; Lippmann, Petra; Ott, Ingo [Journal of Organometallic Chemistry, 2022, vol. 964]
[3]Schmidt, Janina; Wölker, Jessica; Lippmann, Petra; Ott, Ingo [Journal of Organometallic Chemistry, 2022, vol. 964]

18
[ 65020-70-4 ]
[ 670-95-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	With 2-methyl-propan-1-ol; methanesulfonato(2-dicyclohexylphosphino -2’,6’-di-i-propoxy-1,1‘-biphenyl)(2’-amino-1,1’-biphenyl-2-yl)palladium(II); sodium tert-pentoxide In toluene at 80℃; for 96h; Sealed tube; Inert atmosphere;

Reference： [1]Gair, Joseph J.; Grey, Ronald L.; Giroux, Simon; Brodney, Michael A. [Organic Letters, 2019, vol. 21, # 7, p. 2482 - 2487]

19
[ 65020-70-4 ]
5-bromo-4-(4-fluorophenyl)-1-phenyl-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper diacetate; triethylamine; oxygen / dichloromethane / 16 h / 25 °C 2: N-Bromosuccinimide / dichloromethane / 1.25 h / 0 °C

Reference： [1]Current Patent Assignee: MASARYKOVA UNIVERZITA - WO2019/185631, 2019, A1

20
[ 65020-70-4 ]
4-(4-(4-fluorophenyl)-1-phenyl-1H-imidazol-5-_yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper diacetate; triethylamine; oxygen / dichloromethane / 16 h / 25 °C 2: N-Bromosuccinimide / dichloromethane / 1.25 h / 0 °C 3: potassium <i>tert</i>-butylate / 1,4-dioxane; water / 15 h / Reflux

Reference： [1]Current Patent Assignee: MASARYKOVA UNIVERZITA - WO2019/185631, 2019, A1

21
[ 65020-70-4 ]
3-(5-bromo-4-(4-fluorophenyl)-1H-imidazol-1-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper diacetate; triethylamine; dmap / dichloromethane / 17 h / 25 °C 2: N-Bromosuccinimide / dichloromethane / 3 h / 0 °C

Reference： [1]Current Patent Assignee: MASARYKOVA UNIVERZITA - WO2019/185631, 2019, A1

22
[ 65020-70-4 ]
4-(4-(4-fluorophenyl)-1-(pyridin-3-yl)-1H-imidazol-5-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper diacetate; triethylamine; dmap / dichloromethane / 17 h / 25 °C 2: N-Bromosuccinimide / dichloromethane / 3 h / 0 °C 3: sodium methylate; methanesulfonato tri(tert-butyl)phosphine (2'-amino-1,1‘-biphenyl-2-yl) palladium (II) / 1,2-dimethoxyethane; water / 6 h / Reflux

Reference： [1]Current Patent Assignee: MASARYKOVA UNIVERZITA - WO2019/185631, 2019, A1

23
[ 65020-70-4 ]
5-bromo-4-(4-fluorophenyl)imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With N-Bromosuccinimide In tetrahydrofuran; dichloromethane at 0℃; for 1.25h;	51 Preparative Example 51 : 5-bromo-4-(4-fluorophenyl)- imidazole To a cold solution (0 °C) of 4-(4-fluorophenyl)- 1 //-imidazole (106 mg; 0.654 mmol) in dichloromethane/tetrahydrofuran (3 mL + 3 mL) was added /V-bromosuccinimide (122 mg; 0.687 mmol) and the resulting mixture was stirred at 0 °C for 75 minutes. The solvent was evaporated and the residue was purified by column chromatography (ethyl acetate/methanol, 100:1). The product was obtained as a white solid (138 mg, 87 %). (0423) I I NMR (500 MHz, methanol-i/4) d (ppm) 7.80 - 7.60 (m, 3H), 7.25 - 7.15 (m, 2H). (0424) 13C NMR (126 MHz, methanol-i/4) d (ppm) 163.8 (d, 7 = 246.74 Hz), 136.9, 130.0 (d, 7 = 8.30 Hz), 128.4, 116.6 (d, 7 = 21.91 Hz), 112.3. (0425) 19F NMR (471 MHz, methanol-i/4) d (ppm) -115.57. (0426) HRMS calculated for C9H7BrFN2[M+H]+ 240.9771, found 240.9774.

Reference： [1]Current Patent Assignee: MASARYKOVA UNIVERZITA - WO2019/185631, 2019, A1 Location in patent: Page/Page column 45

24
[ 65020-70-4 ]
5-bromo-4-(4-fluorophenyl)-1-(thiophen-3-yl)imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide / tetrahydrofuran; dichloromethane / 1.25 h / 0 °C 2: copper diacetate; triethylamine; dmap / acetonitrile / 22 h / 40 °C

Reference： [1]Current Patent Assignee: MASARYKOVA UNIVERZITA - WO2019/185631, 2019, A1

25
[ 65020-70-4 ]
[ 98-80-6 ]
4-(4-fluorophenyl)-1-phenyl-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With oxygen; copper diacetate; triethylamine In dichloromethane at 25℃; for 16h;	45 Preparative Example 45: 4-(4-fluorophenyl)- 1 -phenyl- 1 //-imidazole To a solution of 4-(4-fluorophenyl)- 1 //-imidazole (440 mg; 2.71 mmol) in dichloromethane (8 mL) were added triethylamine (0.8 mL), phenylboronic acid (496 mg; 4.07 mmol), copper(II) acetate (74 mg; 0.407 mmol) and the resulting mixture was stirred at 25 °C for 16 hours under oxygen atmosphere.The solvent was evaporated in vacuo and the residue was purified by column chromatography (ethyl acetate/hexane, 1: 1). The product was obtained as a white solid (500 mg, 77 %). NMR (500 MHz, CDCl3) d (ppm) 7.92 (d, J = 1.36 Hz, 1H), 7.83 - 7.79 (m, 2H), 7.54 - 7.49 (m, 3H), 7.47 - 7.43 (m, 2H), 7.43 - 7.38 (m, 1H), 7.12 - 7.07 (m, 2H). (0380) 13C NMR (126 MHz, CDCl3) d (ppm) 162.4 (d, / = 245.97 Hz), 142.3, 137.3, 135.8, 130.2, 129.8 (d, J (0381) = 3.18 Hz), 127.9, 126.8 (d, / = 7.98 Hz), 121.6, 115.7 (d, 7 = 21.48 Hz), 113.7. (0382) 19F NMR (471 MHz, CDCl3) d (ppm) -115.15.

Reference： [1]Current Patent Assignee: MASARYKOVA UNIVERZITA - WO2019/185631, 2019, A1 Location in patent: Page/Page column 42

26
[ 329214-79-1 ]
[ 65020-70-4 ]
3-(4-(4-fluorophenyl)-1H-imidazol-1-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With dmap; copper diacetate; triethylamine In dichloromethane at 25℃; for 17h;	48 Preparative Example 48: 3 -(4-( 4-fluorophenyl) - 1 T -imidazol- 1 - vDpyridine To a solution of 4-(4-fluorophenyl)-l//-imidazole (96 mg; 0.592 mmol) in dichloromethane (2.0 mL) were added triethylamine (0.20 mL), 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine (182 mg; 0.888 mmol), DMAP (108 mg; 0.888 mmol), copper(II) acetate (118 mg; 0.651 mmol) and the resulting mixture was stirred at 25 °C for 17 hours.The solvent was evaporated and the residue was purified by column chromatography (dichloromethane/methanol, 12: 1). The product was obtained as a white solid (152 mg, 81 %). (0399) NMR (500 MHz, CDCl3) d (ppm) 9.16 - 8.62 (br m, 2H), 7.95 (s, 1H), 7.85 - 7.75 (m, 3H), 7.62 - 7.45 (br m, 2H), 7.13 - 7.07 (m, 2H). (0400) 13C NMR (126 MHz, CDCfs) d (ppm) 162.5 (d, 7 = 246.29 Hz), 148.94, 148.91, 142.8, 135.7, 129.5 (d, 7 = 2.54 Hz), 128.8, 126.9 (d, 7 = 7.98 Hz), 124.9, 115.8 (d, 7 = 21.59 Hz), 113.5. (0401) 19F NMR (471 MHz, CDCl3) d (ppm) -114.69. (0402) HRMS calculated for Ci4HnFN3[M+H]+ 240.0932, found 240.0930.

Reference： [1]Current Patent Assignee: MASARYKOVA UNIVERZITA - WO2019/185631, 2019, A1 Location in patent: Page/Page column 43-44

27
[ 766-98-3 ]
[ 65020-70-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dodecacarbonyl-triangulo-triruthenium / toluene / 2 h / 100 °C / Inert atmosphere 2: ammonium carbonate / 6 h / 64 °C

Reference： [1]Chen, Yue-Peng; Gu, Ling-Hui; He, Ling; Luo, Yang; Ruan, Yi-Tong; Yang, Ze [Synthesis, 2019, vol. 51, # 18, p. 3520 - 3528]

28
[ 67-56-1 ]
(Z)-1-(4-fluorophenyl)ethene-1,2-diyl diacetate [ No CAS ]
[ 65020-70-4 ]

Yield	Reaction Conditions	Operation in experiment
64%	With ammonium carbonate at 64℃; for 6h;	4-Aryl-1H-imidazoles 8 and 9; General Procedure General procedure: A mixture of (NH4)2CO3 (864 mg, 9 mmol) and 2 (0.45 mmol) in MeOH (5 mL) were stirred at 64 °C for 6 h. Then the solvent was removed in vacuo and the residue was purified by flash chromatography (silica gel, petroleum ether/EtOAc 2:1) to afford product 8.

Reference： [1]Chen, Yue-Peng; Gu, Ling-Hui; He, Ling; Luo, Yang; Ruan, Yi-Tong; Yang, Ze [Synthesis, 2019, vol. 51, # 18, p. 3520 - 3528]

29
tert-butyl 2-bromopropionate [ No CAS ]
[ 65020-70-4 ]
tert-butyl 2-[4-(4-fluorophenyl)imidazol-1-yl]propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 4-(4-fluorophenyl)-1H-imidazole With sodium hydride In tetrahydrofuran for 0.166667h; Cooling with ice; Stage #2: tert-butyl 2-bromopropionate In tetrahydrofuran for 1.5h; Cooling with ice;	1.2 Synthesis of tert-butyl 2-[4-(4-fluorophenyl)imidazol-1-yl]propanoate / Intermediate 38-1 To an ice- cold solution of 4-(4-fluorophenyl)-1H-imidazole (500 mg, 3.08 mmol) in THF (10 mL), NaH (60%, 130 mg, 3.25 mmol) was added. The mixture was stirred for 10 min then tert-butyl 2- bromopropanoate (670 mg, 3.20 mmol) was added and the reaction was stirred for 1.5 h. The mixture was quenched with water, extracted with EtOAc, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (25 g, silica) eluting with 0-100% EtOAc/heptane to yield the title compound (750 mg, 84% yield). 1H NMR (400 MHz, Chloroform-d) δ 7.76 - 7.69 (m, 2H), 7.57 (d, J = 1.3 Hz, 1H), 7.24 (d, J = 1.3 Hz, 1H), 7.08 - 7.01 (m, 2H), 4.73 (q, J = 7.3 Hz, 1H), 1.73 (d, J = 7.3 Hz, 3H), 1.45 (s, 9H). LCMS (Analytical Method D) Rt = 0.97 min, MS (ESIpos): m/z 291.3 [M+H]+, Purity = 100%.

Reference： [1]Current Patent Assignee: FACIO INTELLECTUAL PROPERTY - WO2021/105474, 2021, A1 Location in patent: Page/Page column 58; 83-84

30
[ 1440-61-5 ]
[ 65020-70-4 ]
2-[4-(4-fluorophenyl)-1H-imidazol-1-yl]-1-(morpholin-4-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	Stage #1: 4-(4-fluorophenyl)-1H-imidazole With sodium hydride In tetrahydrofuran for 0.25h; Cooling with ice; Stage #2: N-chloroacetylmorpholine In tetrahydrofuran at 0 - 20℃; for 4h;	1.2 Synthesis of 2-[4-(4-fluorophenyl)-1H-imidazol-1-yl]-1-(morpholin-4-yl)ethan-1-one / Intermediate 43-1 NaH (60%, 95 mg, 2.37 mmol) was added to an ice-cold solution of 4-(4-fluorophenyl)-1H- imidazole (350 mg, 2.16 mmol) in anhydrous THF (7 mL). The reaction was stirred for 15 min before 2-chloro-1-morpholino-ethanone (0.28 mL, 2.16 mmol) was added, and the reaction was stirred at 0 °C for 2 h and at RT for 2 additional h. The reaction was carefully quenched into water, extracted with EtOAc (2x), washed with brine, dried over MgSO4and concentrated in vacuo. The residue was purified by flash chromatography (25 g, silica), eluting with 0-6% MeOH/DCM and the resulting product was triturated with DCM to yield the title compound as a white solid (253 mg, 40% yield). 1H NMR (500 MHz, DMSO-d6) δ 7.79 - 7.73 (m, 2H), 7.59 (d, J = 1.1 Hz, 1H), 7.50 (d, J = 1.1 Hz, 1H), 7.21 - 7.14 (m, 2H), 5.05 (s, 2H), 3.65 (t, J = 4.7 Hz, 2H), 3.60 (t, J = 4.7 Hz, 2H), 3.51 (t, J = 4.6 Hz, 2H), 3.47 (t, J = 4.6 Hz, 2H). LCMS (Analytical Method F) Rt = 0.47 min, MS (ESIpos): m/z 290.1 [M+H]+, Purity = 100%

Reference： [1]Current Patent Assignee: FACIO INTELLECTUAL PROPERTY - WO2021/105474, 2021, A1 Location in patent: Page/Page column 58; 87

31
[ 65020-70-4 ]
2-[4-(4-fluorophenyl)-1H-imidazol-1-yl]propanoic acid trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.17 h / Cooling with ice 1.2: 1.5 h / Cooling with ice 2.1: dichloromethane / 16 h / 20 °C