3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline
3-iodo-4-methylbenzoyl chloride
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Stage #1: 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline; 3-iodo-4-methylbenzoyl chloride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran | 85% |
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h; | 4.60 g |
With N-ethyl-N,N-diisopropylamine; dmap In tetrahydrofuran at 20℃; for 2h; |
3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline
3-iodo-4-toluic acid
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; thionyl chloride; water | 84.3% |
Stage #1: 3-iodo-4-toluic acid With thionyl chloride for 6h; Stage #2: 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline With N-ethyl-N,N-diisopropylamine In chloroform at 60℃; for 5h; | 57% |
Stage #1: 3-iodo-4-toluic acid With thionyl chloride for 1h; Reflux; Stage #2: 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h; |
3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Stage #1: 3-iodo-4-toluic acid With thionyl chloride for 1h; Heating / reflux; Stage #2: 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline With N-ethyl-N,N-diisopropylamine; dmap In tetrahydrofuran; benzene at 20℃; for 2h; |
[3-bromo-5-(trifluoromethyl)phenyl]amine
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethan-1-one; copper(l) iodide; caesium carbonate / N,N-dimethyl-formamide / 18 h / 110 °C / Inert atmosphere; Sealed tube 2: triethylamine / tetrahydrofuran / 1 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: 8-quinolinol; potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 16 h / 40 - 120 °C / Inert atmosphere; Sealed tube 2.1: thionyl chloride / 1 h / Reflux 2.2: 2 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate; copper(l) iodide; 8-quinolinol; ammonia / dimethyl sulfoxide; water / 16 h / 50 - 120 °C / Sealed tube; Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; dmap / tetrahydrofuran; water; thionyl chloride View Scheme | |
Multi-step reaction with 2 steps 1.1: copper(l) iodide; 8-quinolinol / dimethyl sulfoxide / 24 h / 120 °C / Inert atmosphere 2.1: thionyl chloride / 6 h 2.2: 5 h / 60 °C View Scheme |
3-iodo-4-toluic acid
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; thionyl chloride / 2 h / Reflux 2: triethylamine / tetrahydrofuran / 1 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / 2 h / Reflux 2: triethylamine / tetrahydrofuran / 1 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: thionyl chloride / N,N-dimethyl-formamide / 2 h / Reflux 2: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: thionyl chloride 2: tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere View Scheme |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
trimethylsilylacetylene
3-ethynyl-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Stage #1: 3-iodo-4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamide; trimethylsilylacetylene With copper(l) iodide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine In acetonitrile at 80℃; for 2h; Sonogashira Cross-Coupling; Sealed tube; Inert atmosphere; Stage #2: With potassium carbonate In methanol at 20℃; for 3h; | 90% |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
4-pyridin-3-ylpyrimidin-2-ylamine
nilotinib
Conditions | Yield |
---|---|
With caesium carbonate; tris(dibenzylideneacetone)dipalladium (0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane; tert-butyl alcohol at 100℃; for 7h; | 89% |
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane; tert-butyl alcohol at 100℃; for 7h; | 89% |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; palladium dichloride In N,N-dimethyl-formamide at 100℃; for 3h; | 58% |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
3-acetylenylimidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 20℃; for 28.25h; Sonogashira coupling; |
9-vinyl-9H-purine
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
AP24348
Conditions | Yield |
---|---|
With palladium diacetate; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 110℃; for 15h; Heck reaction; Inert atmosphere; |
N-cyclopropyl-9-vinyl-9H-purin-6-amine
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
With palladium diacetate; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 110℃; for 15h; Heck reaction; Inert atmosphere; |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
3-(2-(2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 2 h / 80 °C / Inert atmosphere 2: potassium carbonate; methanol / 3 h / 20 °C 3: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 12 h / 60 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere 2: potassium carbonate / methanol / 3 h / 20 °C 3: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 12 h / 60 °C / Sealed tube; Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere 1.2: 3 h / 20 °C 2.1: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 12 h / 60 °C / Sealed tube; Inert atmosphere View Scheme |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
3-ethynyl-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 2 h / 80 °C / Inert atmosphere 2: potassium carbonate; methanol / 3 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere 2: potassium carbonate / methanol / 3 h / 20 °C View Scheme |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
trimethylsilylacetylene
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In acetonitrile at 80℃; for 2h; Inert atmosphere; | |
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In acetonitrile at 80℃; for 2h; Sealed tube; Inert atmosphere; |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 28.25h; Sealed tube; Inert atmosphere; |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
3-(2-(2-aminopyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere 1.2: 3 h / 20 °C 2.1: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 60 °C / Sealed tube; Inert atmosphere View Scheme |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-(2-(2-(methylamino)pyrimidin-5-yl)ethynyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere 1.2: 3 h / 20 °C 2.1: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 60 °C / Sealed tube; Inert atmosphere View Scheme |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
3-(2-(2-(ethylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere 1.2: 3 h / 20 °C 2.1: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 60 °C / Sealed tube; Inert atmosphere View Scheme |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
3-(2-(2-(isopropylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere 1.2: 3 h / 20 °C 2.1: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 60 °C / Sealed tube; Inert atmosphere View Scheme |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
3-(2-(2-(cyclohexylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere 1.2: 3 h / 20 °C 2.1: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 60 °C / Sealed tube; Inert atmosphere View Scheme |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
3-(2-(2-(tert-butylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere 1.2: 3 h / 20 °C 2.1: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 60 °C / Sealed tube; Inert atmosphere View Scheme |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-(2-(2-(phenylamino)pyrimidin-5-yl)ethynyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere 1.2: 3 h / 20 °C 2.1: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 60 °C / Sealed tube; Inert atmosphere View Scheme |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-(2-(2-(piperidin-1-yl)pyrimidin-5-yl)ethynyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere 1.2: 3 h / 20 °C 2.1: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 60 °C / Sealed tube; Inert atmosphere View Scheme |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere 1.2: 3 h / 20 °C 2.1: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 60 °C / Sealed tube; Inert atmosphere View Scheme |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine; copper(l) iodide / acetonitrile / 2 h / 80 °C / Sealed tube; Inert atmosphere 1.2: 3 h / 20 °C 2.1: palladium diacetate; tricyclohexylphosphine; N-ethyl-N,N-diisopropylamine; copper(l) iodide / N,N-dimethyl-formamide / 60 °C / Sealed tube; Inert atmosphere View Scheme |
3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide
Conditions | Yield |
---|---|
Stage #1: 3-iodo-4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamide; 6-ethynyl-1H-1,8-naphthyridin-2-one With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere; Stage #2: With hydrogenchloride In isopropyl alcohol |
Molecular Structure:
Molecular Formula: C19H15F3IN3O
Molecular Weight: 485.24
Product Name: N-(3-(Trifluoromethyl)-5-(4-methyl-1H-imidazol-1-yl)phenyl)-3-iodo-4-methylbenzamide
Synonyms of N-(3-(Trifluoromethyl)-5-(4-methyl-1H-imidazol-1-yl)phenyl)-3-iodo-4-methylbenzamide (CAS NO.926922-18-1): 3-Iodo-4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamide
CAS NO: 926922-18-1
Melting point: 235-237 °C
Density: 1.61
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