Indometacin CAS 53-86-1 Our advantage 1.Top quality: Using high quality material and establishing a strict quality control system,assigning specific persons in charge of each part of production,from raw material purchase to assembly. 2 Prof
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inquiryHigh quality raw material Indomethacin Description: Indomethacin CAS No.: 53-86-1 MF: C19H15ClNO4 EINECS No.: 200-186-5 Indomethacin, an antiinflammatory agent, inhibits Cox-1 and Cox-2 (cyclooxygenases) w
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inquiryUnique advantages for Indometacin Cas 53-86-1 Guaranteed purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:White or yellow crystalline powder Storage:Store at RT Package:25kg/drum
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inquiryAs a leading and professional manufacturer of APIs and API intermediates in China,Anhui Dexinjia Biopharm Co., Ltd founded in 2006, Except for the R&D center, our company has built a close cooperation relation with Chinese Academy of Sciences,
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Name:Indometacin CAS NO: 53-86-1 Grade:Medical scientific research and export Molecular formula:C19H16ClNO4 Molecular weight: 53-86-1 Product Quality 12 years of chemical raw materials Mature operation of the industry System stability Dat
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inquiryName Indometacin Synonyms 1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid Molecular Formula C19H16ClNO4
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inquiryAppearance:White to off-white powder Storage:ln stock Package:25kg/Barrel Application:Anti-inflammatory, antipyretic effect is obvious, mainly used for rheumatic arthritis, ankylosing photospondylitis, osteoarthritis, etc. that are not easy to toler
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inquiryindomethacin ethyl ester
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water for 1h; Reflux; | 99% |
With lithium hydroxide monohydrate In water at 25℃; for 6h; | 657 mg |
5-Methoxy-2-methylindole-3-acetic acid
4-chloro-benzoyl chloride
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
Stage #1: 5-Methoxy-2-methylindole-3-acetic acid With potassium tert-butylate In tetrahydrofuran at -78℃; for 1h; Large scale; Stage #2: 4-chloro-benzoyl chloride In tetrahydrofuran at 20℃; for 16h; Large scale; | 97% |
Stage #1: 5-Methoxy-2-methylindole-3-acetic acid With potassium tert-butylate In tetrahydrofuran at -78℃; for 1h; Stage #2: 4-chloro-benzoyl chloride In tetrahydrofuran at 20℃; for 16h; | 95% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane 1.) THF; Multistep reaction; |
4-chloro-benzoyl chloride
ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
Stage #1: ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.333333h; Inert atmosphere; Stage #2: 4-chloro-benzoyl chloride In tetrahydrofuran at 25℃; for 10h; Inert atmosphere; Stage #3: With lithium hydroxide monohydrate; water In tetrahydrofuran at 25℃; for 6h; Inert atmosphere; | 92% |
<1-(4-chlorobenzoyl)-2-methyl-5-methoxyindol-3-yl>acetaldehyde
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With N-hydroxyphthalimide; oxygen In acetonitrile at 80℃; for 30h; Schlenk technique; | 91% |
With N-hydroxyphthalimide; oxygen In acetonitrile at 30℃; under 760.051 Torr; for 3h; Schlenk technique; | 91% |
With sodium chlorite; sodium dihydrogenphosphate In tetrahydrofuran; water; tert-butyl alcohol at 20℃; for 0.5h; Schlenk technique; | 78% |
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In tetrahydrofuran; water; tert-butyl alcohol at 20℃; for 0.5h; | 28.4 mg |
2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetic acid benzyl ester
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 0.666667h; | 84% |
With palladium 10% on activated carbon; hydrogen In ethyl acetate | |
With 10% Pd/C; hydrogen In ethyl acetate |
indomethacin methyl ester
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With pyridine; lithium iodide for 20h; Reflux; | 84% |
Stage #1: indomethacin methyl ester With pyridine; lithium iodide for 20h; Reflux; Stage #2: With hydrogenchloride; water at 0℃; | 83% |
With pyridine; lithium iodide for 20h; Reflux; | 83% |
acemetacin tert-butyl ester
B
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With pyridine; iodine; aluminium In acetonitrile at 80℃; for 18h; chemoselective reaction; | A 20% B 70% |
Conditions | Yield |
---|---|
With formic acid In acetic acid for 6h; Heating; | 66% |
acemetacin tert-butyl ester
A
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
B
acemetacin
Conditions | Yield |
---|---|
With iodine; aluminium In acetonitrile at 20℃; for 6h; chemoselective reaction; | A 30% B 66% |
5-methyl-2-furanone
N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine
A
5-Methoxy-2-methylindole-3-acetic acid
B
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With sulfuric acid In acetonitrile for 24h; Fischer indole reaction; Heating; | A n/a B 65% |
4-methoxyphenylhydrazine hydrochloride
4-chloro-benzoyl chloride
levulinic acid
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
Stage #1: 4-methoxyphenylhydrazine hydrochloride With aldehyde resin; triethylamine In dichloromethane at 45℃; Stage #2: 4-chloro-benzoyl chloride With pyridine at 80℃; Stage #3: levulinic acid With trifluoroacetic acid In 1,2-dichloro-ethane at 70℃; | 63% |
Stage #1: 4-methoxyphenylhydrazine hydrochloride With polystyrene aldehyde resin; triethylamine In 1,2-dichloro-ethane at 45℃; Stage #2: 4-chloro-benzoyl chloride With pyridine at 80℃; Stage #3: levulinic acid With trifluoroacetic acid In 1,2-dichloro-ethane at 70℃; |
1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-1H-indolyl-3-essigsaeure-2-oxo-propylester
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With buffer pH 8.0 In 1,4-dioxane; acetonitrile at 57℃; half-life time of hydrolysis at different pH; |
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetoxy]-2'-hydroxy-diethyloxide
A
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
B
diethylene glycol
Conditions | Yield |
---|---|
With isotonic phosphate buffer at 32℃; chemical and enzymatic stability; other temperature and reagents, other pH; other olygoethylene derivatives as substrates; |
Conditions | Yield |
---|---|
With phosphate buffer pH 7.4 In 1,4-dioxane; water at 37℃; for 6h; Rate constant; var. of pH, also in rabbit plasma; |
A
4-hydroxy-benzaldehyde
B
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With water In 1,4-dioxane at 37℃; Rate constant; t1/2; also without alkali; |
Conditions | Yield |
---|---|
With water In 1,4-dioxane at 27℃; Kinetics; Thermodynamic data; other temp.; ΔH (excit.), ΔS (excit.); t1/2; also without alkali; |
[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2,5-dioxo-pyrrolidin-1-ylmethyl ester
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With Tween 80; potassium chloride In phosphate buffer at 37℃; pH=7.4; Kinetics; Further Variations:; pH-values; also in 80 percent human plasma or 10 percent rat liver homogenate; Hydrolysis; |
[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2,3-dioxo-2,3-dihydro-indol-1-ylmethyl ester
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With Tween 80; potassium chloride In phosphate buffer at 37℃; pH=7.4; Kinetics; Further Variations:; pH-values; also in 80 percent human plasma or 10 percent rat liver homogenate; Hydrolysis; |
acemetacin
A
5-Methoxy-2-methylindole-3-acetic acid
B
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
D
para-chlorobenzoic acid
Conditions | Yield |
---|---|
In water at 30℃; Kinetics; Further Variations:; pH-values; Temperatures; |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With water In acetonitrile at 39℃; pH=7.1; Kinetics; |
1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-3-indolylessigsaeure-(2-diethylamino)ethylester
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With pooled human serum at 37℃; Kinetics; |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With pooled human serum at 37℃; Kinetics; |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With pooled human serum at 37℃; Kinetics; |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With pooled human serum at 37℃; Kinetics; |
1-(4-Chlorbenzoyl)-5-methoxy-2-methyl-3-indolylessigsaeure-(2-dimethylamino)ethylester
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With pooled human serum at 37℃; Kinetics; |
sodium 2-(4-methoxyphenyl)diazene-1-sulfonate
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 75 percent / Zn; aq. AcOH / 4 h / 20 °C 2: 88 percent / AcONa / acetic acid / 6 h 3: 66 percent / HCOOH / acetic acid / 6 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: aq. HCl; NaNO2 / 0.5 h / -5 - 0 °C 1.2: 38 g / aq. Na2SO3; NaOH / 0.5 h / 5 °C 2.1: 75 percent / Zn; aq. AcOH / 4 h / 20 °C 3.1: 88 percent / AcONa / acetic acid / 6 h 4.1: 66 percent / HCOOH / acetic acid / 6 h / Heating View Scheme |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 88 percent / AcONa / acetic acid / 6 h 2: 66 percent / HCOOH / acetic acid / 6 h / Heating View Scheme |
N-(4-chlorobenzoyl)-2-iodo-4-methoxyaniline
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 54 percent / tri-2-furylphosphine; CuI; Pd2(dba)3 / Bu4NCl / dimethylformamide / 2 h / 20 °C 2: TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C 3: IBX / ethyl acetate / 2 h / 80 °C 4: 28.4 mg / 2-methyl-2-butene; NaH2PO4*H2O; NaClO2 / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 0.5 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
In methanol at 20℃; | 100% |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; | 100% |
1-hydroxy-pyrrolidine-2,5-dione
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetic acid 2,5-dioxopyrrolidin-1-yl ester
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h; | 99% |
With dicyclohexyl-carbodiimide In DMF (N,N-dimethyl-formamide); dichloromethane at 0 - 20℃; | 92% |
With dicyclohexyl-carbodiimide In 1,4-dioxane for 8h; Ambient temperature; | 91% |
4-hydroxy-benzaldehyde
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; | 99% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 28% |
With pyridine; toluene-4-sulfonic acid; acetic acid; dicyclohexyl-carbodiimide 1.) r.t., 24 h, 2.) 4 deg C, 24 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With oxalyl dichloride In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: With ammonium hydroxide In tetrahydrofuran at 0℃; for 1h; | 99% |
With N-cyclohexyl-N'-(2-morpholinoethyl)carbodiimide para-toluenesulfonate; ammonia; benzotriazol-1-ol In 1,4-dioxane; DMF (N,N-dimethyl-formamide); ethyl acetate at 0 - 20℃; | 95% |
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; ammonium chloride; benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; Substitution; | 84% |
n-Pent-4-enyl alcohol
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
pent-4-en-1-yl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere; | 99% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 40h; Inert atmosphere; | 87% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere; | 84% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h; Schlenk technique; Inert atmosphere; | 30% |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
(4-chlorophenyl)(3-(2-hydroxyethyl)-5-methoxy-2-methyl-1H-indol-1-yl)methanone
Conditions | Yield |
---|---|
With borane-THF In tetrahydrofuran at 5℃; for 18h; | 98% |
With dimethylsulfide borane complex In tetrahydrofuran at 20℃; for 22h; Cooling with ice; | 91% |
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere; | 90% |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With dmap; copper diacetate In acetonitrile at 80℃; for 0.25h; Schlenk technique; Sealed tube; | 98% |
With dmap; copper diacetate In acetonitrile at 80℃; for 3h; Curtius Rearrangement; Inert atmosphere; | 93% |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; | 98% |
ethanol
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
indomethacin ethyl ester
Conditions | Yield |
---|---|
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 16h; | 97% |
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With oxalyl dichloride In dichloromethane at 20℃; for 2h; Stage #2: ethanol With triethylamine In dichloromethane for 0.5h; | 93% |
With toluene-4-sulfonic acid In toluene at 140℃; for 6h; Dean-Stark; | 90% |
(E)-hept-2-en-1-ol
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification; | 97% |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
benzylamine
N-benzyl-2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetamide
Conditions | Yield |
---|---|
With zirconium(IV) chloride In tetrahydrofuran at 70℃; for 24h; Molecular sieve; Inert atmosphere; | 97% |
With (2-iodo-4',5-dimethoxy-[1,1'-biphenyl]-3-yl)boronic acid In dichloromethane at 24 - 25℃; for 6h; Molecular sieve; | 94% |
With (2-bromophenyl)boronic acid In dichloromethane at 25℃; for 48h; Molecular sieve; | 93% |
With bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran at 70℃; for 24h; Molecular sieve; Sealed tube; Inert atmosphere; | 85% |
2-(Trimethylsilyl)ethanol
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
2-(trimethylsilyl)ethyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; Inert atmosphere; | 97% |
isopropyloxycarbonyloxymethyl iodide
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
[(1-methyl)ethoxycarbonyloxy]methyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate
Conditions | Yield |
---|---|
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With N,N,N',N'-tetramethylguanidine In N,N-dimethyl acetamide at -15℃; Inert atmosphere; Stage #2: isopropyloxycarbonyloxymethyl iodide In N,N-dimethyl acetamide at -15℃; Inert atmosphere; | 96.6% |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride
Conditions | Yield |
---|---|
With thionyl chloride In benzene at 65 - 70℃; for 1h; | 96.5% |
With oxalyl dichloride In dichloromethane at 0 - 20℃; for 3.5h; | 96% |
With oxalyl dichloride In dichloromethane at 20℃; for 8h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification; | 96% |
cyclohexylethan-1-ol
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification; | 96% |
3,3-dimethylbutanol
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
3,3-dimethylbutyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
Conditions | Yield |
---|---|
With 3-{[(ethylimino)methylene]-amino}-N,N,N-trimethyl-1-propanaminium iodide; dmap In dichloromethane at 0 - 20℃; Inert atmosphere; | 96% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; Inert atmosphere; | 96% |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With C40H55Cl5N3Pd In toluene at 0℃; for 0.0833333h; Negishi Coupling; Inert atmosphere; Cooling with ice; Stage #2: 1-methylbutylzinc bromide In tetrahydrofuran; toluene at 23℃; for 2h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran for 2h; Stage #2: Cyclopropylamine In tetrahydrofuran at 20℃; for 2h; | 96% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; Steglich Esterification; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; | 96% |
tert-Butyl chloroacetate
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
acemetacin tert-butyl ester
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; sodium carbonate In toluene at 75℃; for 45h; Large scale; | 95.7% |
iodomethyl pivaloate
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
pivaloyloxymethyl 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetate
Conditions | Yield |
---|---|
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With N,N,N',N'-tetramethylguanidine In N,N-dimethyl acetamide at -10 - 20℃; Inert atmosphere; Stage #2: iodomethyl pivaloate In N,N-dimethyl acetamide at -20 - -15℃; | 95.5% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification; | 95% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere; |
2-phenylethanol
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
phenethyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 5h; Esterification; | 95% |
With C10H10Zr(2+)*2CF3O3S(1-)*C4H8O at 80℃; for 24h; Sealed tube; | 70% |
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
2-(5-methoxy-2-methyl-1H-indol-3-yl)acetamide
Conditions | Yield |
---|---|
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With chloroformic acid ethyl ester Stage #2: With ammonium hydroxide; sodium hydroxide | 95% |
Stage #1: [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at -10℃; for 0.5h; Stage #2: With ammonium hydroxide In tetrahydrofuran at 20℃; for 3h; Stage #3: With water; sodium hydroxide In tetrahydrofuran | 88% |
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / 0.17 h / -10 °C 1.2: 0.5 h 2.1: ammonium hydroxide / tetrahydrofuran / 3 h / 20 °C 3.1: sodium hydroxide / tetrahydrofuran View Scheme |
O-<3-Hydroxypropyl>hydroxylamine
[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; | 95% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; | 95% |
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