Conditions | Yield |
---|---|
With hydrogen; platinum on activated charcoal In 1,2-dimethoxyethane under 2585.74 Torr; for 24h; Catalytic hydrogenation; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 52 percent / KF; 18-crown-6 / tetrahydrothiophene 1,1-dioxide / 32 h / 180 °C 2: H2 / 5 percent Pt/C / 1,2-dimethoxy-ethane / 24 h / 2585.74 Torr View Scheme |
2-fluoro-5-chloronitrobenzene
A
2-Fluoroaniline
B
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; hydrazine hydrate In methanol at 80℃; for 0.0833333h; Overall yield = 25 %; |
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
With sodium tetrahydroborate; copper(l) chloride In ethanol at 20℃; | 24 mg |
3,3'-dichloroazobenzene
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 90 °C / Sealed tube 2: sodium tetrahydroborate; copper(l) chloride / ethanol / 20 °C View Scheme |
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: bis(dibenzylideneacetone)-palladium(0); N-fluorobis(benzenesulfon)imide; potassium nitrate / ethyl acetate / 12 h / 100 °C / Sealed tube 2: sodium tetrahydroborate; copper(l) chloride / ethanol / 20 °C View Scheme |
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
With sodium tetrahydroborate; copper(l) chloride In ethanol at 20℃; | 28.8 mg |
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
With iodine; silver sulfate In ethanol at 0 - 20℃; for 1h; Large scale; | 98% |
methyl 3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}-imidazo[1,2-a]pyridin-2-yl)benzoate
5-chloro-2-fluoroaniline
N-(5-chloro-2-fluorophenyl)-3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)benzamide
Conditions | Yield |
---|---|
Stage #1: methyl 3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}-imidazo[1,2-a]pyridin-2-yl)benzoate; 5-chloro-2-fluoroaniline With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With methanol In tetrahydrofuran | 94% |
5-chloro-2-fluoroaniline
4-bromo-5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
With N-Bromosuccinimide In acetonitrile at 25℃; for 1h; | 91% |
Conditions | Yield |
---|---|
for 0.0583333h; microwave irradiation; | 90% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In toluene at 5℃; for 2h; | 88% |
2-(chloromethyl)-8-((2-chloro-5-thiazolyl)methyl)-1,4-dioxa-8-azaspiro[4,5]decane
5-chloro-2-fluoroaniline
N-(5-chloro-2-fluorophenyl)-N-({8-((2-chloro-5-thiazolyl)methyl)-1,4-dioxa-8-aza-spiro[4,5]dec-2-yl}methyl)amine
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 28 - 140℃; | 85% |
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 140℃; for 20h; | 85% |
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 25 - 30℃; for 8h; | 85% |
5-chloro-2-fluoroaniline
(5-Chloro-2-fluoro-phenyl)-hydrazine
Conditions | Yield |
---|---|
With sodium nitrite In hydrogenchloride; water | 83% |
5-chloro-2-fluoroaniline
bis(pinacol)diborane
2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
Conditions | Yield |
---|---|
With tris(trimethylphosphine)nickel(II) chloride; (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride In tetrahydrofuran at 100℃; for 12h; Inert atmosphere; | 81% |
With (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; dichlorobis(trimethylphosphine)nickel In tetrahydrofuran at 100℃; for 12h; Inert atmosphere; Sealed tube; | 81% |
Conditions | Yield |
---|---|
In 1,2-dichloro-benzene; hexan-1-ol for 11h; Heating / reflux; | 76.6% |
C7H6ClN3OS
5-chloro-2-fluoroaniline
1-(5-chloro-2-fluorophenyl)-3-(5-chloro-1,3-dimethyl-1H-pyrazole-4-carbonyl)thiourea
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 4h; | 72.1% |
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 20℃; for 12h; | 72% |
trimethylsilyl isothiocyanate
5-chloro-2-fluoroaniline
para-bromophenacyl bromide
C15H9BrClFN2S*BrH
Conditions | Yield |
---|---|
In ethanol at 70℃; | 69% |
5-chloro-2-fluoroaniline
trifluoroacetic acid
N-(5-chloro-2-hydroxyphenyl)trifluoroacetamide
Conditions | Yield |
---|---|
With Oxone In 1,4-dioxane at 90℃; Schlenk technique; Inert atmosphere; chemoselective reaction; | 66% |
Conditions | Yield |
---|---|
With phosphorus trichloride In chlorobenzene at 130℃; for 0.5h; Microwave irradiation; | 59% |
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 12h; | 52.8% |
5-chloro-2-fluoroaniline
4-chloro-7-methoxy-6-(3-morpholinopropoxy)quinazoline
4-[(5-chloro-2-fluorophenyl)amino]-6-[3-(morpholin-4-yl)propyloxy]-7-methoxyquinazoline
Conditions | Yield |
---|---|
With acetic acid at 80℃; for 7h; | 42% |
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-fluoroaniline With sulfuric acid; sodium nitrite In water at -5 - -2℃; for 0.5h; Stage #2: With sulfuric acid; copper(II) sulfate In water at 160℃; for 2h; | 40% |
Conditions | Yield |
---|---|
With copper(II) sulfate; sodium nitrite In sulfuric acid; water | A n/a B 40% |
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
With formic acid In dichloromethane; isopropyl alcohol at 0 - 20℃; for 0.5h; | 37% |
4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide
5-chloro-2-fluoroaniline
1,1'-carbonyldiimidazole
4-(4-(3-(5-chloro-2-fluorophenyl)ureido)phenoxy)-N-methylpicolinamide
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-fluoroaniline; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 22.1667h; Stage #2: 4-(4-aminophenoxy)-N-methylpyridine-2-carboxamide In dichloromethane for 4h; | 35% |
1-adamantyl isocyanate
5-chloro-2-fluoroaniline
A
N,N'-bis(1-adamantyl)urea
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 20℃; for 12h; Curtius Rearrangement; | A n/a B 35% |
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 20℃; for 12h; | 33% |
2-bromo-3-nitro-benzoic acid
5-chloro-2-fluoroaniline
2-(5-Chloro-2-fluoro-phenylamino)-3-nitro-benzoic acid
Conditions | Yield |
---|---|
With N-ethylmorpholine;; copper; copper(l) chloride In various solvent(s) at 70 - 80℃; for 15h; | 31% |
With N-ethylmorpholine;; copper; copper(l) chloride In various solvent(s) at 70℃; for 18h; Yield given; |
5-(3-hydroxyphenyl)isoxazole-3-carboxylic acid
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
Stage #1: 5-(3-hydroxyphenyl)isoxazole-3-carboxylic acid With thionyl chloride In tetrahydrofuran for 0.5h; Reflux; Stage #2: 5-chloro-2-fluoroaniline With triethylamine In tetrahydrofuran at 20 - 35℃; for 2h; | 24% |
5-chloro-2-fluoroaniline
N-(5-chloro-2-fluorophenyl)iminodiacetic acid
Conditions | Yield |
---|---|
22% |
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane; XPhos In tetrahydrofuran; dichloromethane at 65℃; for 1h; Sealed tube; | 21% |
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
Stage #1: 5-(3-hydroxy-4-methoxyphenyl)isoxazole-3-carboxylic acid With thionyl chloride In tetrahydrofuran for 0.5h; Reflux; Stage #2: 5-chloro-2-fluoroaniline With triethylamine In tetrahydrofuran at 20 - 35℃; for 2h; | 20% |
1-(azidomethyl)-4-methoxybenzene
5-chloro-2-fluoroaniline
Conditions | Yield |
---|---|
Stage #1: 1-(azidomethyl)-4-methoxybenzene; 3-fluoro-4-(3,3,3-trifluoroprop-1-yn-1-yl)pyridine In tert-butyl methyl ether; tert-butyl alcohol at 80℃; for 2h; Stage #2: 5-chloro-2-fluoroaniline With potassium carbonate In dimethyl sulfoxide at 180℃; for 5h; Stage #3: With trifluoroacetic acid at 50℃; | 17% |
Conditions | Yield |
---|---|
In dichloromethane at -4 - 20℃; Molecular sieve; | A 9.9% B 11.7% |
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