adapalene
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; for 22h; | 100% |
3-(1-adamantyl)-4-methoxyphenylboronic acid
6-bromo-2-naphthoic acid
adapalene
Conditions | Yield |
---|---|
Stage #1: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 6-bromo-2-naphthoic acid With potassium carbonate; palladium 10% on activated carbon In tetrahydrofuran; water for 8h; Heating / reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran for 1h; Product distribution / selectivity; | 99% |
Stage #1: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 6-bromo-2-naphthoic acid With potassium hydroxide; 5%-palladium/activated carbon In tetrahydrofuran; water at 55℃; for 2h; Heating / reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 20℃; pH=6 - 7; Product distribution / selectivity; | 99% |
Stage #1: 3-(1-adamantyl)-4-methoxyphenylboronic acid; 6-bromo-2-naphthoic acid With potassium carbonate; palladium diacetate; CyJohnPhos In tetrahydrofuran; water for 2 - 4h; Suzuki Coupling; Heating / reflux; Stage #2: With hydrogenchloride; water In tetrahydrofuran for 1h; Product distribution / selectivity; | 94.8% |
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester
adapalene
Conditions | Yield |
---|---|
Stage #1: 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester With ethylene glycol; sodium hydroxide Stage #2: With hydrogenchloride In water Product distribution / selectivity; | 97% |
Stage #1: 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester With ethylene glycol; sodium hydroxide Stage #2: With hydrogenchloride In water Product distribution / selectivity; | 96% |
With water; sodium hydroxide In propylene glycol | 89% |
adapalene
Conditions | Yield |
---|---|
With acetic acid In tetrahydrofuran; water at 60 - 70℃; Heating / reflux; | 95% |
With hydrogenchloride In water pH=3 - 4; Product distribution / selectivity; | 80% |
(6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)methanol
adapalene
Conditions | Yield |
---|---|
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In dichloromethane at 20℃; for 24h; | 94% |
Conditions | Yield |
---|---|
With potassium fluoride; propylene glycol; chloro-[2-(9-phenyl-1,10-phenanthrolin-2-yl)phenyl]palladium In dichloromethane at 100℃; for 12h; Inert atmosphere; | 93% |
adapalene
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water at 40℃; for 1.5h; | 89.29% |
With hydrogenchloride In 1,4-dioxane; methanol; water | |
With hydrogenchloride In water Product distribution / selectivity; |
ethyl 6 (3-adamantyl-4-methoxyphenyl)-2-naphthoate
adapalene
Conditions | Yield |
---|---|
Stage #1: ethyl 6 (3-adamantyl-4-methoxyphenyl)-2-naphthoate With sodium hydroxide In tetrahydrofuran; ethanol at 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; ethanol for 1h; Reflux; | 70% |
carbon dioxide
adapalene
Conditions | Yield |
---|---|
Stage #1: 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-bromonaphthalene With tert.-butyl lithium; sodium hydride In tetrahydrofuran; pentane at -60 - 20℃; for 0.666667h; Stage #2: carbon dioxide In tetrahydrofuran; pentane at -60 - 20℃; for 1.5h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; pentane for 0.166667h; Product distribution / selectivity; | 41% |
Stage #1: 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-bromonaphthalene With n-butyllithium; sodium hydride In tetrahydrofuran; hexane at -40 - 20℃; for 0.666667h; Stage #2: carbon dioxide In tetrahydrofuran; hexane at -40 - 20℃; for 1.5h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane for 0.166667h; Product distribution / selectivity; | 30% |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 86 percent / conc. H2SO4 / CH2Cl2 / 8 h / Ambient temperature 2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h 3: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane 4: 81 percent / 2 N NaOH / methanol / 8 h / Heating View Scheme |
1-adamanthanol
adapalene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 86 percent / conc. H2SO4 / CH2Cl2 / 8 h / Ambient temperature 2: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h 3: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane 4: 81 percent / 2 N NaOH / methanol / 8 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: sulfuric acid; acetic acid / 48 h / 20 °C 2: potassium carbonate / acetone / 8 h / Reflux 3: magnesium / tetrahydrofuran / 1 h / 40 °C 4: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C 5: sodium hydroxide / methanol / 8 h / Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C 2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 3.2: 1.25 h / Heating / reflux 3.3: 2.17 h 4.1: sodium hydroxide; water / tetrahydrofuran; 1,4-dioxane / 6 h / 90 °C / Heating / reflux 5.1: hydrogenchloride / water / pH 3 - 4 View Scheme | |
Multi-step reaction with 5 steps 1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C 2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 3.2: 1.25 h / Heating / reflux 3.3: 2.17 h 4.1: potassium hydroxide; water / 1,4-dioxane / 2.25 - 4.25 h / Heating / reflux 5.1: hydrogenchloride / water View Scheme |
2-(1-adamantyl)-4-bromophenol
adapalene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 20 deg C, 2 h 2: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane 3: 81 percent / 2 N NaOH / methanol / 8 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 8 h / Reflux 2: magnesium / tetrahydrofuran / 1 h / 40 °C 3: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C 4: sodium hydroxide / methanol / 8 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: bis(pinacol)diborane; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 100 °C 1.2: 80 - 100 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 2.2: 1.5 h / 20 °C 3.1: sodium hydroxide / methanol / 8 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 2.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 2.2: 1.25 h / Heating / reflux 2.3: 2.17 h 3.1: sodium hydroxide; water / tetrahydrofuran; 1,4-dioxane / 6 h / 90 °C / Heating / reflux 4.1: hydrogenchloride / water / pH 3 - 4 View Scheme | |
Multi-step reaction with 4 steps 1.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 2.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 2.2: 1.25 h / Heating / reflux 2.3: 2.17 h 3.1: potassium hydroxide; water / 1,4-dioxane / 2.25 - 4.25 h / Heating / reflux 4.1: hydrogenchloride / water View Scheme |
2-(1-adamantyl)-4-bromoanisole
adapalene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) Mg, I2, 2.) ZnCl2, 3.) NiCl2*1,2-bis(diphenylphosphino)ethane 2: 81 percent / 2 N NaOH / methanol / 8 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: magnesium / tetrahydrofuran / 1 h / 40 °C 2: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C 3: sodium hydroxide / methanol / 8 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: n-butyllithium 2: 21 h / Flow reactor 3: sodium hydroxide; water / propylene glycol View Scheme |
methyl 6-bromo-2-naphthoate
adapalene
Conditions | Yield |
---|---|
Stage #1: 3-adamantyl-4-methoxyphenyl potassium trifluoroborate; methyl 6-bromo-2-naphthoate With potassium hydroxide; 5%-palladium/activated carbon In tetrahydrofuran; water for 10.25h; Suzuki Miyaura coupling; Heating / reflux; Stage #2: With hydrogenchloride; water |
3-(1-adamantyl)-4-methoxyphenylboronic acid
methyl 6-bromo-2-naphthoate
adapalene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: sodium hydroxide / methanol / 8 h / Reflux View Scheme |
3-(1-adamantyl)-4-methoxybenzene magnesium bromide
adapalene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C 2: sodium hydroxide / methanol / 8 h / Reflux View Scheme |
adapalene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sulfuric acid / toluene / 12 h / 78 °C / Inert atmosphere 2.1: sulfuric acid / chloroform / 20 °C 3.1: sodium hydroxide / tetrahydrofuran; ethanol / 20 °C 3.2: 1 h / Reflux View Scheme |
ethyl 6-(4-methoxyphenyl)-2-naphthoate
adapalene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sulfuric acid / chloroform / 20 °C 2.1: sodium hydroxide / tetrahydrofuran; ethanol / 20 °C 2.2: 1 h / Reflux View Scheme |
4-bromo-phenol
adapalene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sulfuric acid; acetic acid / 48 h / 20 °C 2: potassium carbonate / acetone / 8 h / Reflux 3: magnesium / tetrahydrofuran / 1 h / 40 °C 4: bis-triphenylphosphine-palladium(II) chloride; zinc(II) chloride / 0.75 h / 55 °C 5: sodium hydroxide / methanol / 8 h / Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C 2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 3.2: 1.25 h / Heating / reflux 3.3: 2.17 h 4.1: sodium hydroxide; water / tetrahydrofuran; 1,4-dioxane / 6 h / 90 °C / Heating / reflux 5.1: hydrogenchloride / water / pH 3 - 4 View Scheme | |
Multi-step reaction with 5 steps 1.1: sulfuric acid; acetic acid / 4.17 h / 20 - 70 °C 2.1: potassium carbonate / acetone / 4.25 - 6.25 h / 20 °C / Heating / reflux 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 0.5 h / 20 - 40 °C / Heating / reflux 3.2: 1.25 h / Heating / reflux 3.3: 2.17 h 4.1: potassium hydroxide; water / 1,4-dioxane / 2.25 - 4.25 h / Heating / reflux 5.1: hydrogenchloride / water View Scheme |
6-bromo-2-naphthoic acid
adapalene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: palladium 10% on activated carbon; sodium carbonate / methanol; water / 78 °C / Inert atmosphere 2.1: sulfuric acid / toluene / 12 h / 78 °C / Inert atmosphere 3.1: sulfuric acid / chloroform / 20 °C 4.1: sodium hydroxide / tetrahydrofuran; ethanol / 20 °C 4.2: 1 h / Reflux View Scheme |
methyl 6-bromo-2-naphthoate
adapalene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium hydroxide / methanol / 8 h / 50 °C 2.1: palladium 10% on activated carbon; sodium carbonate / methanol; water / 78 °C / Inert atmosphere 3.1: sulfuric acid / toluene / 12 h / 78 °C / Inert atmosphere 4.1: sulfuric acid / chloroform / 20 °C 5.1: sodium hydroxide / tetrahydrofuran; ethanol / 20 °C 5.2: 1 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: bis(pinacol)diborane; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / 1,4-dioxane / 100 °C 1.2: 80 - 100 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 2.2: 1.5 h / 20 °C 3.1: sodium hydroxide / methanol / 8 h / Reflux View Scheme |
Conditions | Yield |
---|---|
In glycerol | |
In glycerol | |
In glycerol |
6-(3-adamantan-1-yl-4-hydroxyphenyl)naphthalene-2-carboxylic acid methyl ester
adapalene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C 1.2: 1.5 h / 20 °C 2.1: sodium hydroxide / methanol / 8 h / Reflux View Scheme |
adapalene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium phosphate tribasic trihydrate; bis(triphenylphosphine)nickel(II) chloride; 1-n-butyl-3-methylimidazolim bromide / toluene / 6 h / 110 °C / Inert atmosphere 2: sulfuric acid / chloroform / 20 °C 3: sodium hydroxide / tetrahydrofuran; water / 6 h / Reflux View Scheme |
4-methoxyphenylboronic acid
adapalene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium phosphate tribasic trihydrate; bis(triphenylphosphine)nickel(II) chloride; 1-n-butyl-3-methylimidazolim bromide / toluene / 6 h / 110 °C / Inert atmosphere 2: sulfuric acid / chloroform / 20 °C 3: sodium hydroxide / tetrahydrofuran; water / 6 h / Reflux View Scheme |
ethanamine hydrochloride
adapalene
ethylamide of 6-[3-(1-adamantyl)-4-methoxyphenyl]2-naphthoic acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; | 100% |
adapalene
(6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalen-2-yl)methanol
Conditions | Yield |
---|---|
Stage #1: adapalene With borane-THF In tetrahydrofuran at 0 - 20℃; for 3h; Stage #2: With water In tetrahydrofuran | 98% |
With borane-THF In tetrahydrofuran at 0 - 20℃; for 3h; | 98% |
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 2h; | 79% |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; |
adapalene
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 98% |
adapalene
Conditions | Yield |
---|---|
With dmap; trifluoromethyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Schlenk technique; | 95% |
5-methyloxazole-2-carboxylic acid ethyl ester
adapalene
Conditions | Yield |
---|---|
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 92% |
Conditions | Yield |
---|---|
With iron(III) chloride; triphenylphosphine In tetrahydrofuran at 20℃; for 0.5h; chemoselective reaction; | 91% |
N-hydroxyphthalimide
adapalene
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; for 2h; Schlenk technique; Inert atmosphere; | 90% |
With dicyclohexyl-carbodiimide In ethyl acetate at 20℃; for 3h; Inert atmosphere; | 21% |
Conditions | Yield |
---|---|
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 87% |
1-Methylbenzimidazole
adapalene
Conditions | Yield |
---|---|
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 85% |
phosphonic acid diethyl ester
adapalene
Conditions | Yield |
---|---|
With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Inert atmosphere; Schlenk technique; | 83% |
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox; | 72% |
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane for 18h; Inert atmosphere; Schlenk technique; Heating; | 72% |
1-methyl-1H-imidazole
adapalene
Conditions | Yield |
---|---|
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 81% |
N,N-Dimethylacrylamide
adapalene
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; 2,2-dimethylpropanoic anhydride; bis[2-(diphenylphosphino)phenyl] ether; sodium chloride In tetrahydrofuran at 150℃; for 10h; Heck Reaction; Schlenk technique; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3h; Inert atmosphere; | 79.3% |
adapalene
diazomethyl-trimethyl-silane
6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran; methanol at 0 - 20℃; for 1h; | 79% |
adapalene
Conditions | Yield |
---|---|
With dmap; copper diacetate In dimethyl sulfoxide at 100℃; for 6h; Schlenk technique; Sealed tube; Inert atmosphere; | 77% |
N-(2-methylbenzoyl)-8-aminoquinoline
adapalene
Conditions | Yield |
---|---|
With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; fluoro-N,N,N′,N′-bis(tetramethylene)formamidinium hexafluorophosphate In 1,4-dioxane at 140℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Molecular sieve; | 76% |
adapalene
Conditions | Yield |
---|---|
With dipotassium hydrogenphosphate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; 2,4,6-Triisopropylthiophenol; water-d2; triphenylphosphine In dichloromethane at 20℃; for 36h; Inert atmosphere; Irradiation; Schlenk technique; Sealed tube; | 73% |
With dipotassium hydrogenphosphate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; 2,4,6-Triisopropylthiophenol; water-d2; triphenylphosphine In dichloromethane at 20℃; for 36h; Irradiation; Inert atmosphere; Sealed tube; | 73% |
Diphenylphosphine oxide
adapalene
Conditions | Yield |
---|---|
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 115℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox; | 68% |
With di-tert-butyl dicarbonate; N,N-dimethyl-cyclohexanamine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate In 1,4-dioxane at 115℃; for 18h; Inert atmosphere; Schlenk technique; | 68% |
2-phenyl-1,3,4-oxadiazole
adapalene
Conditions | Yield |
---|---|
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 68% |
3,3,3-trifluoro-2-phenylpropene
adapalene
Conditions | Yield |
---|---|
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; sodium hydrogencarbonate; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 48h; Molecular sieve; Inert atmosphere; Sealed tube; Irradiation; | 67% |
adapalene
carbonic acid 1,1-dimethyl-3-phenyl-prop-2-ynyl ester methyl ester
Conditions | Yield |
---|---|
With potassium phosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In N,N-dimethyl acetamide at 110℃; regiospecific reaction; | 51% |
Molecular Structure of Adapalene (CAS NO. 106685-40-9):
IUPAC Name: 6-[3-(1-Adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
Molecular Formula: C28H28O3
Molecular Weight: 412.520120 g/mol
Index of Refraction: 1.654
Molar Refractivity: 122.61 cm3
Molar Volume: 334.3 cm3
Surface Tension: 54.9 dyne/cm
Density: 1.233 g/cm3
Flash Point: 205.9 °C
Enthalpy of Vaporization: 94.76 kJ/mol
Boiling Point: 606.3 °C at 760 mmHg
Vapour Pressure: 1.49E-15 mmHg at 25 °C
Melting Point: 319-322 °C
Product Categories: APIs; Adamantane derivatives; Antiacne; Intermediates & Fine Chemicals; Pharmaceuticals
Friedel-Crafts condensation of 4-bromophenol (I) with 1-adamantanol (II) in the presence of H2SO4 yielded the adamantyl phenol (III). Subsequent alkylation of the sodium phenoxide of (III) with iodomethane produced the methyl ether (IV). The Grignard reagent (V), prepared from aryl bromide (IV), was converted to the organozincate derivative, and then subjected to a nickel-catalyzed cross-coupling with methyl 6-bromo-2-naphthoate (VI) to furnish adduct (VII). The target carboxylic acid was finally obtained by saponification of the methyl ester (VII).
Content: ≥99.5%
The total miscellaneous: ≤0.5%
Single-Miscellaneous: ≤0.1%
Size: ≤50μm
Adapalene with cas registry number of 106685-40-9 is white crystalline solid, also called Adapalene [USAN:INN:BAN] ; 6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoic acid ; Adapalen ; Adapaleno ; Adapaleno [INN-Spanish] ; Adapalenum ; Adapalenum [INN-Latin] ; CD 271 ; Differin ; UNII-1L4806J2QF ; 2-Naphthalenecarboxylic acid, 6-(4-methoxy-3-tricyclo(3.3.1.1(sup 3,7))dec-1-ylphenyl)- . Adapalene (CAS NO. 106685-40-9) is used in the treatment of the face, chest and back acne, and Adapalene can alleviate the response to the cell-mediated inflammatory.
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