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Product Details of [ 176961-53-8 ]

CAS No. :176961-53-8 MDL No. :MFCD04114653
Formula : C9H7BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :IRIGPPDONXVEHU-UHFFFAOYSA-N
M.W : 223.07 Pubchem ID :11694265
Synonyms :

Safety of [ 176961-53-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 176961-53-8 ]

* 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 [ 176961-53-8 ]

[ 176961-53-8 ] Synthesis Path-Downstream   1~45

  • 1
  • [ 176961-13-0 ]
  • [ 176961-53-8 ]
  • 4'-(1<i>H</i>-imidazol-2-yl)-biphenyl-2-sulfonic acid (3,4-dimethyl-isoxazol-5-yl)-(2-methoxy-ethoxymethyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene
  • 2
  • [ 206535-83-3 ]
  • [ 176961-53-8 ]
YieldReaction ConditionsOperation in experiment
83% With [bis(acetoxy)iodo]benzene; potassium carbonate In dimethyl sulfoxide at 20℃; for 24h;
78% With oxygen; pyrographite In xylene at 120℃; for 25h;
  • 3
  • 2-(4-bromo-phenyl)-imidazolidine [ No CAS ]
  • [ 176961-53-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: K2CO3; I2 / 2-methyl-propan-2-ol / 3 h / 70 °C 2: 83 percent / (diacetoxyiodo)benzene; K2CO3 / dimethylsulfoxide / 24 h / 20 °C
  • 4
  • [ 1122-91-4 ]
  • [ 176961-53-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2-methyl-propan-2-ol / 20 °C 2: K2CO3; I2 / 2-methyl-propan-2-ol / 3 h / 70 °C 3: 83 percent / (diacetoxyiodo)benzene; K2CO3 / dimethylsulfoxide / 24 h / 20 °C
  • 5
  • [ 176961-53-8 ]
  • N-(3,4-Dimethyl-5-isoxazolyl)-4'-(1H-imidazol-2-yl)[1,1'-biphenyl]-2-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (Ph3P)4Pd; aq. Na2CO3 / ethanol; toluene 2: 6N aq. HCl / ethanol
  • 6
  • [ 661-69-8 ]
  • [ 176961-53-8 ]
  • [ 1021919-39-0 ]
YieldReaction ConditionsOperation in experiment
46% In toluene at 100℃; for 2h; 5.1.154.A [00643] A. 2-(4-(Trimethylstannyl)phenyl)-lH-imidazole. A solution of 2-(4- bromophenyl)-lH-imidazole (1.0 g, 4.48 mmol), hexamethylditin (1.08 mL, 4.93 mmol), tetrakis(triphenylphosphine)palladium(0) (0.508 g, 0.06 mmol) in toluene (15 mL) was heated at 100 °C for 2 h. Upon completion of the reaction, toluene was removed under reduced pressure, and the residue was purified by Biotage chromatography (0-40% EtOAc in hexanes) to afford the desired stannane (635 mg, 46%). MS (ESI) m/z 309.2[M+l]+.
  • 7
  • [ 107-15-3 ]
  • [ 586-75-4 ]
  • [ 176961-53-8 ]
YieldReaction ConditionsOperation in experiment
83% With H6[PMo9V3O40] In acetonitrile at 90℃;
  • 8
  • [ 288-32-4 ]
  • [ 106-40-1 ]
  • [ 176961-53-8 ]
YieldReaction ConditionsOperation in experiment
53.61% Stage #1: 4-bromo-aniline With hydrogenchloride; sodium nitrite In water at 0 - 10℃; Stage #2: 1H-imidazole With sodium acetate at 5 - 20℃;
Stage #1: 4-bromo-aniline With hydrogenchloride; sodium azide In water at 0 - 10℃; Stage #2: 1H-imidazole With sodium acetate In water at 5 - 20℃; for 51h;
  • 9
  • [ 623-00-7 ]
  • [ 176961-53-8 ]
YieldReaction ConditionsOperation in experiment
IV.22 2-(4-bromophenyl)-1H-imidazole Example IV-22 2-(4-bromophenyl)-1H-imidazole The title compound was prepared from p-bromobenzonitrile as described for the preparation Example IV-21, with the exception that purification of the title compound consisted of a combination of recrystallization (i-PrOH) and flash chromatography (EtOAc/hexanes). LC/MS (method A) tR 1.25 min, m/z 223, 225 (M+H, Br isotopes).
IV.22 2-(4-bromophenyl)-1H-imidazole Example IV-22 2-(4-bromophenyl)-1H-imidazole The title compound was prepared from p-bromobenzonitrile as described for the preparation Example IV-21, with the exception that purification of the title compound consisted of a combination of recrystallization (i-PrOH) and flash chromatography (EtOAc/hexanes). LC/MS (method A) tR 1.25 min, m/z 223, 225 (M+H, Br isotopes).
  • 10
  • [ 73183-34-3 ]
  • [ 176961-53-8 ]
  • [ 1229584-17-1 ]
YieldReaction ConditionsOperation in experiment
36% With potassium acetate In dimethyl sulfoxide at 80℃; 167 2-(4-Bromo-phenyl)-lH-imidazole (300 mg, 1.3 mmol), bis(pinacolato)diboron (376 mg, 1.48 mmol), KOAc (400 mg, 4.03 mmol) and PdCl2(dppf) CH2Cl2 (50 mg, 0.067 mmol) were combined in DMSO (8 ml) and stirred t 800C overnight. EtOAc was added, washed with water, dried, evaporated and purified by silica gel chromatography eluting with 0-5% MeOH:DCM to give 116 mg (36%) of the title compound. 1H NMR (CDCl3, 300 MHz): δ 7.86 (s, 4H), 7.18 (s, 2H), 1.36 (s, 12H).
36% With potassium acetate In dimethyl sulfoxide at 80℃; 167 Preparation of 2-[4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenyl]-lH-imidazole (Intermediate CG)[0394] 2-(4-Bromo-phenyl)-lH-imidazole (300 mg, 1.3 mmol), bis(pinacolato)diboron (376 mg, 1.48 mmol), KOAc (400 mg, 4.03 mmol) and PdCl2(dppf) CH2Cl2 (50 mg, 0.067 mmol) were combined in DMSO (8 ml) and stirred t 80°C overnight. EtOAc was added, washed with water, dried, evaporated and purified by silica gel chromatography eluting with 0-5 % MeOH:DCM to give 116 mg (36%) of the title compound. 1H NMR (CDC13, 300 MHz): δ 7.86 (s, 4H), 7.18 (s, 2H), 1.36 (s, 12H).
36% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 80℃; 167 Preparation of Intermediate A: 2-[4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)- phenyl]-lH-imidazole In reference to Scheme 29, 2-(4-Bromo-phenyl)-lH-imidazole (300 mg, 1.3 mmol), bis(pinacolato)diboron (376 mg, 1.48 mmol), KOAc (400 mg, 4.03 mmol) and PdCl2(dppf) CH2Cl2 (50 mg, 0.067 mmol) were combined in DMSO (8 ml) and stirred t 80°C overnight. EtOAc was added, washed with water, dried, evaporated and purified by silica gel chromatography eluting with 0-5% MeOH:DCM to give 116 mg (36%) of the title compound. XH NMR (CDC13, 300 MHz): δ 7.86 (s, 4H), 7.18 (s, 2H), 1.36 (s, 12H).
  • 11
  • [ 24424-99-5 ]
  • [ 176961-53-8 ]
  • [ 176961-27-6 ]
YieldReaction ConditionsOperation in experiment
96% With dmap In tetrahydrofuran for 1h; 21.1 2-(4-Bromophenyl)imidazole (330 mg, 1.48 mmol) was suspended in TΗF (1OmL) and DMAP (194 mg, 1.59 mmol) then di-tert-butyl dicarbonate (366 mg, 1.68 mmol) were sequentially added. The mixture was stirred for Ih then concentrated and partitioned with ethyl acetate and 10% aqueous citric acid. The organic solution was washed with brine, dried over anhydrous sodium sulfate then filtered and concentrated to afford 1,1- dimethylethyl 2-(4-bromophenyl)-lΗ-imidazole-l-carboxylate (457 mg, 96% yield) as an oil.
  • 12
  • [ 176961-53-8 ]
  • [ 543-27-1 ]
  • [ 1256956-07-6 ]
YieldReaction ConditionsOperation in experiment
46% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 0.5h; 4.5 2-(4-bromophenyl)imidazole (5.3 g, 23.76 mmol) was taken into THF (100 mL) followed by addition of DIPEA (5 mL, 28.5 mmol) and isobutyl chloro formate (3.4 niL, 26.1 mmol) and the resulting solution was stirred for 30 minutes at room temperature. The solution was then concentrated and the residue partitioned with ethyl acetate and water. The organic phase was washed once with 10% aqueous citric acid, brine then dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (2.5:1 hexanes:ethyl acetate) to give isobutyl 2-(4-bromophenyl)-lH- imidazole-1-carboxylate (3.5 g, 46% yield) as an amorphous residue.
  • 13
  • [ 76513-69-4 ]
  • [ 176961-53-8 ]
  • [ 934744-50-0 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 2-(4-bromophenyl)-1H-imidazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 20℃; for 2h;
80% Stage #1: 2-(4-bromophenyl)-1H-imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h; Inert atmosphere; 22 2-(4-Bromophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole To a solution of 2-(4-bromophenyl)-1H-imidazole (1 equiv) in DMF (0.47 M) was added sodium hydride (3 equiv, 60% in mineral oil) at 0° C. under nitrogen. After the resulting reaction mixture was stirred at 0° C. for 15 min, (2-(chloromethoxy)-ethyl)trimethylsilane (1.1 equiv) was added. Then the mixture was stirred at room temperature for 3 h and quenched with saturated aqueous ammonium chloride solution. The aqueous layer was extracted with DCM. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. Concentration under vacuum gave the crude product, which was purified by silica gel column chromatography (25% ethyl acetate in petroleum ether) to afford the title compound (80% yield). MS (ESI) m/z 354.2 [M+1]+.
70% Stage #1: 2-(4-bromophenyl)-1H-imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 24h; 1.6 To a solution of 2-(4-bromophenyl)-lH-imidazole (15.0 g, 67.2 mmol) in DMF (150 ml) at 0 °C was added NaH (60% dispersion in mineral oil, 3.90 g, 97.5mmol). The mixture was stirred at 0 °C for 1 hour and (2-(chloromethoxy)ethyl)trimethylsilane (14.8 mL, 84.0 mmol) was added. The resulting solution was allowed to warm from 0 °C to ambient temperature while stirring over 24 hours. The reaction mixture was diluted with 1 : 1 brine:H20 (500 mL), extracted with EtOAc (3 x 200 mL), dried over sodium sulfate, filtered and concentrated to an oil. Purification of the oil by column chromatography, eluting with 10-50% EtOAc/Hexane, afforded 2-(4-bromophenyl)-l-((2-(trimethylsilyl)ethoxy)methyl)- lH-imidazole as a light orange oil, (17.1 g, 70%). LCMS (APCI+) m/z 353, 355 [M+H]+.
With potassium carbonate In N,N-dimethyl-formamide Inert atmosphere; 34 Synthesis of 2-(4-bromophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H- imidazole (34B): To a solution of 2-(4-bromophenyl)-1H-imidazole in 5 mL of DMF, potassium carbonate (1.25 g, 9.1 mmol) and 2-(trimethylsilyl)ethoxymethyl chloride (1.51 g, 9.1 mmol) were added. The reaction was stirred overnight. The reaction was diluted with EtOAc (100 mL) and washed with water (50 mL) and brine (50 mL). The organic layer was separated and was concentrated to dryness in vacuo to afford compound 34B, which was without further purification. MS (m/z) 353 [M+H]+.

  • 14
  • [ 623-00-7 ]
  • [ 22483-09-6 ]
  • [ 176961-53-8 ]
YieldReaction ConditionsOperation in experiment
20% Stage #1: 4-bromobenzenecarbonitrile With sodium methylate In methanol at 20℃; for 5.5h; Stage #2: 2,2-dimethoxyethylamine With acetic acid In methanol at 50℃; for 1h; Stage #3: With hydrogenchloride In methanol at 65℃; for 18h; 1.5 To a solution of 4-bromobenzonitrile (80.0 g, 440 mmol) in MeOH(800 mL) was added NaOMe (20.1 mL, 87.9 mmol). The mixture was allowed to stir at ambient temperature for 5.5 hours. 2,2-Dimethoxyethanamine (61.6 mL, 571 mmol) was added followed by acetic acid (50.3 mL, 879 mmol). The reaction mixture was heated to 50 °C for 1 hour and then cooled to ambient temperature. MeOH (200 mL) and HC1 (200 mL, 1200 mmol) were added, and the reaction mixture was heated to 65 °C for 18 hours. The reaction mixture was then concentrated, and washed with 1 :1 H20:Et20 (2000 mL). The pH of the aqueous layer was adjusted to pH = 9 with 6 N NaOH. The resulting solid was filtered and dried to give 2-(4-bromophenyl)-lH-imidazole (20.0 g, 20%). LCMS (APCI+) m/z 223, 224 [M+H]+.
  • 15
  • [ 176961-53-8 ]
  • [ 1269646-23-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C 1.2: 24 h / 0 - 20 °C 2.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; (diphenylphosphin)ferrocene / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 2 h / 20 °C 2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 110 °C / Inert atmosphere
  • 16
  • [ 176961-53-8 ]
  • [ 1269646-25-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C 1.2: 24 h / 0 - 20 °C 2.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; (diphenylphosphin)ferrocene / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 3.1: sodium carbonate / tris-(dibenzylideneacetone)dipalladium(0); XPhos / 1,4-dioxane / 72 h / 90 °C / Inert atmosphere; sealed tube
  • 17
  • [ 176961-53-8 ]
  • [ 1269643-37-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C 1.2: 24 h / 0 - 20 °C 2.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; (diphenylphosphin)ferrocene / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 3.1: sodium carbonate / tris-(dibenzylideneacetone)dipalladium(0); XPhos / 1,4-dioxane / 72 h / 90 °C / Inert atmosphere; sealed tube 4.1: trifluoroacetic acid / dichloromethane / 12 h / 20 °C
  • 18
  • [ 176961-53-8 ]
  • [ 1269643-42-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C 1.2: 24 h / 0 - 20 °C 2.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; (diphenylphosphin)ferrocene / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 3.1: sodium carbonate / tris-(dibenzylideneacetone)dipalladium(0); XPhos / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere; sealed vessel 4.1: trifluoroacetic acid / dichloromethane / 12 h / 20 °C
  • 19
  • [ 176961-53-8 ]
  • C30H32N6O3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C 1.2: 24 h / 0 - 20 °C 2.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; (diphenylphosphin)ferrocene / 1,4-dioxane / 18 h / 90 °C / Inert atmosphere 3.1: sodium carbonate / tris-(dibenzylideneacetone)dipalladium(0); XPhos / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere; sealed vessel
  • 20
  • [ 131543-46-9 ]
  • [ 1122-91-4 ]
  • [ 176961-53-8 ]
YieldReaction ConditionsOperation in experiment
75% With ammonium acetate; lipase In water at 45℃; for 2h; Enzymatic reaction; 3.2. General procedures for the synthesis of unsubstituted imidazoles General procedure: A mixture of glyoxal (0.058 g), benzaldehyde (0.106 g), ammonium acetate (0.154 g),and lipase (0.05 g) were taken in a 50-ml, two-necked, round-bottomed flask. Thereaction mixture was stirred for 1-4 h at 45 C. in 10 ml water. After completion ofthe reaction as indicated by thin-layer chromatography (TLC; ethyl acetate/n-hexane,2:1), the reaction mixture was filtered and washed with water (310 ml), and thesolid residue was crystallized from ethyl acetate to give pure product 3a as white solid. All other products were prepared following this procedure and were identifiedby their melting point, 1H NMR comparing to the literature.
19.5% With ammonium hydroxide In ethanol; water at 0 - 20℃; 8.3. General procedure the synthesis of 2-aryl-1H-imidazole (18, 5a and 5b) General procedure: To a solution of appropriate benzaldehyde (17, 4a, and 4b, 14-28 g, 100 mmol) in ethanol (400 ml) at 0 °C was added a solution of 40% oxalaldehyde in water (16 g, 110 mmol) and a solution of 29% ammonium hydroxide in water (120 g, 1000 mmol). After stirring for 2-3 days at room temperature, the reaction mixture was concentrated, and the residue was subjected to flash column chromatography with dichloromethane as eluent to yield the titled compound as a yellow powder. Yield: 10-30%.
19.5% With ammonium hydroxide In ethanol; water at 0 - 20℃; 5; 11.a To a solution of appropriate benzaldehyde (81, and 8g, 100 mmol) in ethanol (400 mL) at 0 °C was added a solution of 40% oxalaldehyde (glyoxal) in water (1.1 equiv) and a solution of 29% ammonium hydroxide in water (10 equiv). After stirring for 2- 3 days at RT, the reaction mixture was concentrated and the residue was subjected to flash column chromatography with dichloromethane as eluent to yield the titled compound as a yellow powder. Yield: 10%- 30%.
19.5% With ammonium hydroxide In ethanol; water at 20℃; 2 General procedure: [002361 Synthesis of 91, 9g: To a solution of appropriate benzaldehyde (81, and 8g, 100mmol) in ethanol (400 mL) at 0 °C was added a solution of 40% oxalaldehyde (glyoxal) in water(1.1 equiv) and a solution of 29% ammonium hydroxide in water (10 equiv). After stuffing for 2-387 days at RT, the reaction mixture was concentrated and the residue was subjected to flash column chromatography with dichloromethane as eluent to yield the titled compound as a yellow powder. Yield: 10%- 30%.
With ammonium hydroxide In ethanol; water at 0 - 20℃; for 48h;

  • 21
  • [ 98-09-9 ]
  • [ 176961-53-8 ]
  • [ 1332526-28-9 ]
YieldReaction ConditionsOperation in experiment
61.2% Stage #1: 2-(4-bromophenyl)-1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; 8.5. General procedure for the synthesis of 2-aryl-1-(phenylsulfonyl)-1H-imidazole (6a-b, 19), 1-(phenylsulfonyl)-1H-indole (10a-f, 10h), and 1-(phenylsulfonyl)-1H-benzo[d]imidazole (10g) General procedure: To a solution of imidazoles (5a, 5b, 18), indoles (9a-f, 9h), or benzimidazole (9g) (1.3-3.5 g, 10 mmol) in anhydrous THF (200 ml) at 0 °C was added sodium hydride (60% dispersion in mineral oil, 48 mg, 12 mmol) and stirred for 20 min. 4-Methoxy-benzenesulfonyl chloride (2.5 g, 12 mmol) (for 6b) or benzenesulfonyl chloride (2.1 g, 12 mmol) (for others) was added, and the reaction mixture was stirred overnight. After dilution by 200 ml of saturated NaHCO3 solution (aqueous), the reaction mixture was extracted by ethyl acetate (600 ml). The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (hexane/ethyl acetate, 2:1) to give a pale solid. Yield: 40-95%.
61.2% Stage #1: 2-(4-bromophenyl)-1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil 5; 11.b To a solution of imidazoles (91, 9g) (10 mmol) in anhydrous THF (200 mL) at 0 °C was added sodium hydride (60% dispersion in mineral oil, 1.2 equiv) and stirred for 20 min. 4-Methoxybenzenesulfonyl chloride (for lOgb) or benzenesulfonyl chloride (for others)(1.2 equiv) was added and the reaction mixture was stirred overnight. After dilution by 200 mL of saturated NaHCC>3 solution (aqueous), the reaction mixture was extracted by ethyl acetate (600 mL). The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (hexane: ethyl acetate 2: 1) to give a pale solid. Yield: 40 -95 .
61.2% Stage #1: 2-(4-bromophenyl)-1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil 2 General procedure: [002371 Synthesis of lOla, 10gb: To a solution of imidazoles (91, 9g) (10 mmol) inanhydrous THF (200 mL) at 0 °C was added sodium hydride (60% dispersion in mineral oil, 1.2equiv) and stirred for 20 mi 4-Methoxybenzenesulfonyl chloride (for 10gb) or benzenesulfonyl chloride (for others)(1.2 equiv) was added and the reaction mixture was stirred overnight. After dilution by 200 mL of saturated NaHCO3 solution (aqueous), the reaction mixture was extracted by ethyl acetate (600 mL). The organic layer was dried over magnesium sulfate and concentrated.The residue was purified by flash column chromatography (hexane: ethyl acetate 2:1) to give a pale solid. Yield: 40%-95%.
  • 22
  • [ 176961-53-8 ]
  • [ 1332526-30-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.17 h / Inert atmosphere 2.2: -78 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C 2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.17 h / -78 °C 2.2: -78 °C
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere 2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.17 h / -78 °C / Inert atmosphere 2.2: -78 °C
  • 23
  • [ 176961-53-8 ]
  • [ 1332526-32-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.17 h / Inert atmosphere 2.2: -78 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C 2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.17 h / -78 °C 2.2: -78 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C / Inert atmosphere 2.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.17 h / -78 °C / Inert atmosphere 2.2: -78 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
  • 24
  • [ 1021918-89-7 ]
  • [ 176961-53-8 ]
  • [ 1021916-67-5 ]
YieldReaction ConditionsOperation in experiment
3% With trans-bis(triphenylphosphine)palladium dichloride In N,N-dimethyl-formamide at 90℃; for 1.5h; 6-(4-(1H-Imidazol-2-yl)phenyl)-1-(cyclohexylmethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (44) 1-(Cyclohexylmethyl)-6-(trimethylstannyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (200 mg, 0.506 mmol), 1-(4-bromophenyl) imidazole (94 mg, 0.42 mmol), dichlorobis(triphenylphosphine)palladium(II) (104 mg, 0.10 mmol) in DMF (10 mL) were reacted for 1.5 h at 90 °C. The product was purified by reverse-phase semi-preparatory HPLC (30-100% acetonitrile + 0.1% TFA in H2O + 0.1% TFA, over 30 min). The desired fractions were concentrated, the residue was taken up in DMSO (2 mL) and heated at 100 *°C until completely dissolved. Water was added upon cooling and the desired product precipitated out of solution. The precipitate was collected by vacuum filtration, washed with water and dried under high vacuum to provide the desired product (5 mg, 3% yield) as a tan solid.
  • 25
  • [ 176961-53-8 ]
  • [ 1229583-68-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dimethyl sulfoxide / 80 °C 2: sodium carbonate / bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 72 h / 60 °C
Multi-step reaction with 2 steps 1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / dimethyl sulfoxide / 80 °C 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 48 h / 60 °C
  • 27
  • [ 274692-06-7 ]
  • [ 176961-53-8 ]
  • 1,1-dimethylethyl (3S)-3-[2-(4-bromophenyl)-1H-imidazol-1-yl]methyl}-1-pyrrolidinecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% Stage #1: 2-(4-bromophenyl)-1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.333333h; Inert atmosphere; Stage #2: tert-butyl (S)-3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate In tetrahydrofuran; mineral oil at 0 - 80℃; 21.b b) 1,1 -dimethylethyl (35)-3 - { [2-(4-bromophenyl)- 1 H-imidazol- 1 -yljmethyl} - 1 - pyrrolidinecarboxylateA flask containing 2-(4-bromophenyl)-lH-imidazole (1.345 mmol) and NaH (60% dispersion in mineral oil, 1.614 mmol) under nitrogen was cooled to 0 °C and treated with dry THF (2 mL). After 20 min, a solution of 1,1 -dimethylethyl 3-[(methylsulfonyl)oxy]methyl}-l -pyrrolidinecarboxylate (1.345 mmol) in dry THF (2 mL) was added to the reaction mixture and the mixture was allowed to warm to roomtemperature. After stirring overnight at room temperature (minor product formed), the reaction mixture was heated at 80 °C overnight (-70% conversion). The reaction mixture was then partitioned between EtOAc and dilute NaHCC"3 solution and the aqueous layer was further extracted twice with EtOAc. The combined organic layers were dried over Na2S04 and were concentrated. Purification of the residue by flash chromatography (1-10% ethanol/EtOAc) and then repurification of impure product by flash chromatography (1% ethanol/EtOAc) gave the title compound (243 mg, 44%>) as a colorless solid. LCMS (ES+) m/z 406, 408 [M+H]+.
  • 28
  • [ 1122-91-4 ]
  • [ 107-15-3 ]
  • [ 176961-53-8 ]
YieldReaction ConditionsOperation in experiment
92% With tribromide-modified silica-coated magnetic nanoparticles (Fe3O4/SiO2/(CH2)3N+Me3Br3) In neat (no solvent) at 80℃; for 0.2h; Green chemistry; 2.3. General procedure for the synthesis of imidazole, benzimidazole, benzothiazole, and perimidine derivatives General procedure: A stirred solution of the substrate (1 mmol), aryl adehyde (1 mmol),and tribromide-modified silica-coated magnetic nanoparticles (Fe3O4/SiO2/(CH2)3N+Me3Br3-, 0.007 g) was heated 80 °C. After completion of the reaction [TLC (AcOEt/hexane 1:3) monitoring], EtOH (10 mL) was added. The catalyst was recovered by an external magnet, and thereaction mixture was poured into ice-water (30 mL). The solid productwas filtered, washed with ice-water, and dried.
88% With potassium ferrocyanide In water at 20℃; for 0.233333h;
72.1% Stage #1: 4-bromo-benzaldehyde; ethylenediamine With iodine; potassium carbonate In <i>tert</i>-butyl alcohol at 70℃; for 3.5h; Inert atmosphere; Stage #2: With [bis(acetoxy)iodo]benzene; potassium carbonate; 2-(p-tolyl)imidazole In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; 8L.1 Step-i.• Synthesis of 2 -(4-bromophenyl)-i H-imidazole (Compound 8€-i): a) In a 250 mL round bottom flask, a solution of 4-bromobenzladehyde (3.0 g, 16.21 mmol) in t-BuOH (150 mL) was treated with ethylenediamine (1.2 mL, 17.83 mmol). The mixture was stirred at RT under an argon atmosphere for 30 mm, and then K2C03 (6.7 ig, 48.64 mmol) and iodine (5.12 g, 20.27 mmol) were added to the mixture and stirred at 70 °C. After 3 h, the mixture was quenched with saturated aqueous Na2SO3 until the iodine color almost disappeared, and was extracted with CHC13. The organic extract was washed with saturated aqueous NaHCO3, brine and dried over anhydrous Na2SO4. The solution was concentrated under reduced pressure to yield the product (2.51 g crude). The crude material was used in the next step without further purification.b) In a 250 mL round bottom flask, a mixture of 2-(4-methylphenyl)imidazoline (2.5 g, 11.46 mmol) and K2C03 (1.75 g, 12.61 mmol) in DMSO (10 mL) was treated with PhI(OAc)2 (4.06 g, 12.61 mmol). The mixture was stirred for 24 h at RT under an argon atmosphere. Upon completion of reaction (TLC), the reaction mixture was diluted with saturated aqueous NaHCO3 and EtOAc. The mixture was stirred for 5 mm at RT, before separating the organic layer and drying over anhydrous Na2SO4. The solution was concentrated under reduced pressure to afford the title compound. Yield: 1.81 g (72.1%).‘H NMR (400 MHz, DMSO-d6) ö 12.60 (brs, 1H), 7.87 (d, J= 8.0 Hz, 2H), 7.64 (d, J= 8.4 Hz, 2H), 7.28 (s, 1H), 7.04 (s, 1H).LCMS (ESI+, m/z): 223.0, 225.1 (M+H).
  • 29
  • [ 76513-69-4 ]
  • [ 176961-53-8 ]
  • [ 1269646-23-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 2 h / 100 °C
YieldReaction ConditionsOperation in experiment
45.4% With [bis(acetoxy)iodo]benzene; potassium carbonate In dimethyl sulfoxide at 20℃; for 12h; Inert atmosphere; 2I.2 Synthesis of 2-(4-(trifluoromethyl)phenyl)-lH-imidazole General procedure: In a 250 mL round bottom flask, a stirred solution 2-(4-(trifluoromethyl)phenyl)-4,5- dihydro- lH-imidazole (5.0 g, 23.36 mmol) in DMSO (80 mL) was treated with K2C03 (3.55 g, 25.7 mmol) and (diacetoxyiodo)benzene (8.30 g, 25.7 mmol) at RT under nitrogen atmosphere. The reaction mixture was stirred at RT for 12 h under nitrogen atmosphere. Upon completion of reaction (TLC), the reaction mixture was diluted with ice cold water and extracted with ethyl acetate (100 mL x 3). The combined organic extract was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (elution, 40% EtOAc in hexanes) to afford the title compound as a yellow solid (2.70 g, 54.7%) (0267) 1H NMR (400 MHz, DMSO-d6): δ 12.81 (brs, 1H), 8.14 (d, J = 8.8 Hz, 2H), 7.81 (d, J = 8.8 Hz, 2H), 7.23 (s, 2H). (0268) 19F NMR (400 MHz, DMSO-d6) : δ -60.98 LCMS (ESI+, m/z): 213.0 (M+H)+.
With formic acid at 80℃; for 1h; IV-22 2-(3-Bromophenyl)-1H-imidazole General procedure: A solution of N-[2,2-bis(ethyloxy)ethyl]-3-bromobenzenecarboximidamide (2.85 g; 9.04 mmol; Step 2 above) in HCO2H (15 mL) was heated at 80° C. for 1 h and concentrated in vacuo (2×PhMe chase). The residue was purified by flash chromatography (MeOH/NH4OH/CH2Cl2), affording the title compound as a light pink solid.
  • 31
  • [ 1007579-18-1 ]
  • [ 176961-53-8 ]
  • 1,1-dimethylethyl (4,4-dimethylcyclohexyl)[2-({4′-(1H-imidazol-2-yl)-4-biphenylyl}oxy)ethyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 1.17h; Inert atmosphere; VI-5 General procedure: A mixture of 1,1-dimethylethyl {2-[(4-bromophenyl)oxy]ethyl}(4,4-dimethylcyclohexyl)carbamate (0.085 g; 0.20 mmol; Example V-8), [4-(acetylamino)phenyl]boronic acid (0.040 g; 0.22 mmol), PdCl2(dppf).CH2Cl2(0.005 g; 0.006 mmol), Na2CO3(2 mL of a 2M solution) and DME (2 mL) was sparged with N2for 10 minutes at room temperature and heated at 80° for 1 h (until consumption of the aryl bromide, as judged by LC/MS). Upon cooling, the mixture was partitioned between EtOAc/H2O, layers were separated and the aqueous layer was extracted with EtOAc (×2). Combined organics were washed (brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a pale yellow solid. Aryl bromide IV-22 and aryl boronate V-18 used. Pd(PPh3)4 used as catalyst
  • 32
  • [ 176961-53-8 ]
  • [ 1618658-98-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 2 h / 20 °C 2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 110 °C / Inert atmosphere 3.1: water; 1,4-dioxane / 15 h / 75 °C / Alkaline conditions 4.1: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating 5.1: trifluoroacetic acid / dichloromethane / 20 °C 5.3: 20 - 50 °C
  • 33
  • [ 176961-53-8 ]
  • 2-chloro-4-(cyclopentyloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-5-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 2 h / 20 °C 2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 110 °C / Inert atmosphere 3.1: water; 1,4-dioxane / 15 h / 75 °C / Alkaline conditions
  • 34
  • [ 176961-53-8 ]
  • 4-(4-(cyclopentyloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-5-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-3-methoxy-N-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 1.2: 2 h / 20 °C 2.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 110 °C / Inert atmosphere 3.1: water; 1,4-dioxane / 15 h / 75 °C / Alkaline conditions 4.1: 1,4-dioxane / 1.5 h / Alkaline conditions; Inert atmosphere; Sealed tube; Heating
  • 35
  • [ 19226-36-9 ]
  • [ 176961-53-8 ]
  • 8-bromo-5-phenylimidazo[1,2-c]quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With silver hexafluoroantimonate; bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)]; glacial acetic acid In 1,2-dichloro-ethane at 120℃; for 24h; Schlenk technique; Sealed tube;
74% With silver hexafluoroantimonate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide In 1,2-dichloro-ethane at 120℃;
  • 36
  • [ 176961-53-8 ]
  • [ 502636-15-9 ]
  • 9-bromo-5-phenethyl-5H-benzo[c]imidazo[1,2-a]azepine-6-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In dichloromethane at 100℃; for 10h; regioselective reaction;
68% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In dichloromethane at 100℃; for 10h; Sealed tube; 23 Example 23 Into a 15mL pressure tube, sequentially add 1g (66.9 mg, 0.3 mmol), dichloromethane (3 mL), 2a (84.7 mg, 0.45 mmol), dichloro (pentamethylcyclopentadienyl) rhodium (III) dimer (4.7 mg, 0.0075 mmol) and silver acetate (100.1 mg, 0.6 mmol), then the pressure-resistant tube was sealed and placed in a 100 ° C. oil bath for 10 h. After the reaction was completed, the mixture was cooled to room temperature, filtered with suction, dried, and separated through a silica gel column (dichloromethane / methanol / acetic acid = 30/1 / 0.1) to obtain 3g (83.5 mg, 68%) as a white solid product.
  • 37
  • [ 536-38-9 ]
  • [ 176961-53-8 ]
  • 1-(4-chlorophenyl)-2(2-(4-bromophenyl)-1H-imidazol-1-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In N,N-dimethyl-formamide at 5 - 20℃; for 51h; Preparation of diaryl imidazolyl ethanones 2 General procedure General procedure: To 2-(aryl)-1H-imidazole 1 (0.002 mol), 0.002 mol of appropriately substituted phenacyl bromide in 1.9 mL of dimethylformamide was added and stirred for 3 h at 5-10°C followed by stirring for 48 h at room temperature. The reaction mixture was poured into ice water and the resulting precipitate was filtered. The solid mass was treated with ethanol and filtered. The filtrate on concentration yielded white crystals of 2. Spectral data
  • 38
  • [ 99-73-0 ]
  • [ 176961-53-8 ]
  • 1-(4-bromophenyl)-2(2-(4-bromophenyl)-1H-imidazol-1-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% In N,N-dimethyl-formamide at 5 - 20℃; for 51h; Preparation of diaryl imidazolyl ethanones 2 General procedure General procedure: To 2-(aryl)-1H-imidazole 1 (0.002 mol), 0.002 mol of appropriately substituted phenacyl bromide in 1.9 mL of dimethylformamide was added and stirred for 3 h at 5-10°C followed by stirring for 48 h at room temperature. The reaction mixture was poured into ice water and the resulting precipitate was filtered. The solid mass was treated with ethanol and filtered. The filtrate on concentration yielded white crystals of 2. Spectral data
  • 39
  • [ 59142-68-6 ]
  • [ 176961-53-8 ]
  • 2-bromo-4-(2-(4-bromophenyl)-1H-imidazol-1-yl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
5% With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 0.25h; Microwave irradiation;
  • 40
  • [ 176961-53-8 ]
  • tert-butyl 4-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / Inert atmosphere 2: 2,2'-bis(diphenylphosphino)biphenyl; sodium tertiary butoxide; tris-(dibenzylideneacetone)dipalladium(0) / toluene / Reflux; Inert atmosphere
  • 41
  • [ 176961-53-8 ]
  • 1-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)piperazine 2,2,2-trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / Inert atmosphere 2: 2,2'-bis(diphenylphosphino)biphenyl; sodium tertiary butoxide; tris-(dibenzylideneacetone)dipalladium(0) / toluene / Reflux; Inert atmosphere 3: 0.5 h / Inert atmosphere
  • 42
  • [ 176961-53-8 ]
  • tert-butyl (S)-(1-(2-(4-(4-(1H-imidazol-2-yl)phenyl)piperazin-1-yl)-6-bromothiazolo[4,5-b]pyridin-5-yl)-2-(3,5-difluorophenyl)ethyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / Inert atmosphere 2.1: 2,2'-bis(diphenylphosphino)biphenyl; sodium tertiary butoxide; tris-(dibenzylideneacetone)dipalladium(0) / toluene / Reflux; Inert atmosphere 3.1: 0.5 h / Inert atmosphere 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / Inert atmosphere 4.2: 6 h / Inert atmosphere 4.3: Inert atmosphere
  • 43
  • [ 176961-53-8 ]
  • tert-butyl (S)-(1-(2-(4-(4-(1H-imidazol-2-yl)phenyl)piperazin-1-yl)-6-(3-oxoisoindolin-5-yl)thiazolo[4,5-b]pyridin-5-yl)-2-(3,5-difluorophenyl)ethyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / Inert atmosphere 2.1: 2,2'-bis(diphenylphosphino)biphenyl; sodium tertiary butoxide; tris-(dibenzylideneacetone)dipalladium(0) / toluene / Reflux; Inert atmosphere 3.1: 0.5 h / Inert atmosphere 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / Inert atmosphere 4.2: 6 h / Inert atmosphere 4.3: Inert atmosphere 5.1: Sodium hydrogenocarbonate; (bis(tricyclohexyl)phosphine)palladium(II) dichloride / 1,4-dioxane / 0.17 h / 130 °C / Microwave irradiation; Inert atmosphere
  • 44
  • [ 176961-53-8 ]
  • N-((S)-1-(2-(4-(4-(1H-imidazol-2-yl)phenyl)piperazin-1-yl)-6-(3-oxoisoindolin-5-yl)thiazolo[4,5-b]pyridin-5-yl)-2-(3,5-difluorophenyl)ethyl)-2-((3bS,4aR)-5,5-difluoro-3-(trifluoromethyl)-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / Inert atmosphere 2.1: 2,2'-bis(diphenylphosphino)biphenyl; sodium tertiary butoxide; tris-(dibenzylideneacetone)dipalladium(0) / toluene / Reflux; Inert atmosphere 3.1: 0.5 h / Inert atmosphere 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / Inert atmosphere 4.2: 6 h / Inert atmosphere 4.3: Inert atmosphere 5.1: Sodium hydrogenocarbonate; (bis(tricyclohexyl)phosphine)palladium(II) dichloride / 1,4-dioxane / 0.17 h / 130 °C / Microwave irradiation; Inert atmosphere 6.1: hydrogenchloride / 1,4-dioxane / 1 h / Inert atmosphere 7.1: N-ethyl-N,N-diisopropylamine; 1-[(1-(cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylaminomorpholinomethylene)]methanaminium hexafluorophosphate / N,N-dimethyl-formamide; 1,4-dioxane / 1.5 h / 20 °C / Inert atmosphere
  • 45
  • [ 176961-53-8 ]
  • C35H30F2N8OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / Inert atmosphere 2.1: 2,2'-bis(diphenylphosphino)biphenyl; sodium tertiary butoxide; tris-(dibenzylideneacetone)dipalladium(0) / toluene / Reflux; Inert atmosphere 3.1: 0.5 h / Inert atmosphere 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / Inert atmosphere 4.2: 6 h / Inert atmosphere 4.3: Inert atmosphere 5.1: Sodium hydrogenocarbonate; (bis(tricyclohexyl)phosphine)palladium(II) dichloride / 1,4-dioxane / 0.17 h / 130 °C / Microwave irradiation; Inert atmosphere 6.1: hydrogenchloride / 1,4-dioxane / 1 h / Inert atmosphere
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