etoricoxib hydrochloride
etoricoxib
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In dichloromethane; water at 10 - 20℃; for 0.5h; Reagent/catalyst; Large scale; | 96.5% |
methyl iodide
etoricoxib
Conditions | Yield |
---|---|
Stage #1: 4-(5-chloro-6'-methyl-[2,3'-bipyridin]-3-yl)benzenesulfinic acid With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 65℃; for 0.333333h; Stage #2: methyl iodide In tetrahydrofuran at 65℃; for 2h; Cooling with liquid nitrogen; | 95% |
5-chloro-3-(4-methylsulphonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine
etoricoxib
Conditions | Yield |
---|---|
With sodium molybdate; sulfuric acid; dihydrogen peroxide In methanol at 55℃; for 0.25h; | 94% |
With oxygen; uranyl(VI) acetate dihydrate In o-xylene; water; acetonitrile at 20℃; under 760.051 Torr; Schlenk technique; Irradiation; | 91% |
With diethylene glycol dibutyl ether; oxygen at 110℃; for 20h; Green chemistry; | 78% |
1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone
etoricoxib
Conditions | Yield |
---|---|
With potassium hydroxide In acetonitrile at 80℃; for 8h; Concentration; Inert atmosphere; | 89% |
With caesium carbonate In tetrahydrofuran at 20℃; for 3h; | 82% |
1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone
etoricoxib
Conditions | Yield |
---|---|
Stage #1: 1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 0.25h; Inert atmosphere; Stage #2: N-(2-chloro-3-(dimethylamino)allylidene)-N-methylmethanaminium hexafluorophosphate(V) With acetic acid In tetrahydrofuran at 20 - 25℃; for 2.5h; Inert atmosphere; Stage #3: With ammonium hydroxide In tetrahydrofuran at 60 - 65℃; for 1.5h; Inert atmosphere; | 84.4% |
With methanesulfonic acid; ammonium acetate; propionic acid In toluene at 25 - 75℃; for 14 - 16h; Reflux; |
2,5-dichloro-3-[4-(methylsulfonyl)phenyl]pyridine
etoricoxib
Conditions | Yield |
---|---|
palladium | 79% |
1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone
etoricoxib
Conditions | Yield |
---|---|
Stage #1: 1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone With potassium tert-butylate In tetrahydrofuran at 25 - 30℃; for 1h; Stage #2: 2-chloro-1,3-(bis-piperidinyl)trimethinium hexafluorophosphate In tetrahydrofuran at 30 - 55℃; Product distribution / selectivity; | 75.9% |
formamide
1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone
etoricoxib
Conditions | Yield |
---|---|
With methanesulfonic acid In 1,2-dichloro-ethane at 80 - 100℃; for 24h; | 73% |
etoricoxib
Conditions | Yield |
---|---|
With ammonium hydroxide In tetrahydrofuran at 60 - 65℃; Inert atmosphere; | 72.1% |
With ammonium hydroxide In tetrahydrofuran for 5h; cyclocondensation; Heating; |
(6-methylpyridin-3-yl)boronic acid
etoricoxib
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,4-dioxane; water at 80℃; for 8h; Suzuki Coupling; chemoselective reaction; | 71% |
5-bromo-2-methylpyridine
etoricoxib
Conditions | Yield |
---|---|
With di-tert-butyl(methyl)phosphonium tetrafluoroborate salt; palladium diacetate; caesium carbonate In 1,4-dioxane at 120℃; for 18h; Inert atmosphere; | 69% |
1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone
etoricoxib
Conditions | Yield |
---|---|
With methanesulfonic acid; propionic acid In toluene at 114℃; for 12h; Heating / reflux; | 65% |
1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone
A
3,5-dichloropyridine
B
etoricoxib
Conditions | Yield |
---|---|
With ammonium acetate In propionic acid at 125℃; | A n/a B 62% C 15% |
(6-methylpyridin-3-yl)boronic acid
etoricoxib
Conditions | Yield |
---|---|
With palladium diacetate; sodium hydrogencarbonate; tricyclohexylphosphine In 1,4-dioxane; water at 80℃; for 1.5h; Suzuki-Miyaura Coupling; Sealed tube; Inert atmosphere; Schlenk technique; | 60% |
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere; Schlenk technique; Sealed tube; | 52% |
2,3-dichloroacrolein
etoricoxib
Conditions | Yield |
---|---|
Stage #1: 2,3-dichloroacrolein; Lithium; (Z)-2-(4-methanesulfonyl-phenyl)-1-(6-methyl-pyridin-3-yl)-ethenolate In tetrahydrofuran Stage #2: With ammonia In tetrahydrofuran Heating; Further stages.; | 58% |
2-bromo-5-chloro-3-(4-(methylsulfonyl)phenyl)pyridine
(6-methylpyridin-3-yl)boronic acid
etoricoxib
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); cesium fluoride In 1,4-dioxane for 20h; Concentration; Suzuki Coupling; Inert atmosphere; Reflux; | 55% |
4-methanesulphonylphenylboronic acid
etoricoxib
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane at 100℃; | 54% |
1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone
etoricoxib
Conditions | Yield |
---|---|
With ammonium acetate In propionic acid Heating; | 47% |
etoricoxib
Conditions | Yield |
---|---|
With ammonium hydroxide In tetrahydrofuran for 3h; Heating; | 8.42 g |
2-methyl-5-formylpyridine
etoricoxib
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 46.5 g / isopropyl acetate / 60 °C 2: 46.5 g / isopropyl acetate / 60 - 65 °C 3: t-BuOK / propan-2-ol; tetrahydrofuran / 0.5 h / 25 °C 4: 24.91 g / aq. HCl / 25 - 45 °C 5: t-BuOK / tetrahydrofuran / 0.75 h / 20 °C 6: AcOH; TFA / tetrahydrofuran / 0.75 h / 25 - 30 °C 7: 8.42 g / aq. NH4OH / tetrahydrofuran / 3 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: 46.5 g / isopropyl acetate / 60 °C 2: 46.5 g / isopropyl acetate / 60 - 65 °C 3: t-BuOK / propan-2-ol; tetrahydrofuran / 0.5 h / 25 °C 4: 24.91 g / aq. HCl / 25 - 45 °C 5: 62 percent / NH4OAc / propionic acid / 125 °C View Scheme | |
Multi-step reaction with 5 steps 1: 46.5 g / isopropyl acetate / 60 °C 2: 46.5 g / isopropyl acetate / 60 - 65 °C 3: t-BuOK / propan-2-ol; tetrahydrofuran / 0.5 h / 25 °C 4: 24.91 g / aq. HCl / 25 - 45 °C 5: 47 percent / NH4OAc / propionic acid / Heating View Scheme |
Methyl 6-methylnicotinate
etoricoxib
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 58 percent / t-BuMgCl / tetrahydrofuran / 50 °C 2: t-BuOK / tetrahydrofuran / 0.75 h / 20 °C 3: AcOH; TFA / tetrahydrofuran / 0.75 h / 25 - 30 °C 4: 8.42 g / aq. NH4OH / tetrahydrofuran / 3 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 58 percent / t-BuMgCl / tetrahydrofuran / 50 °C 2: 62 percent / NH4OAc / propionic acid / 125 °C View Scheme | |
Multi-step reaction with 2 steps 1: 58 percent / t-BuMgCl / tetrahydrofuran / 50 °C 2: 47 percent / NH4OAc / propionic acid / Heating View Scheme |
4-(methylsulfonyl)phenylacetic acid
etoricoxib
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 58 percent / t-BuMgCl / tetrahydrofuran / 50 °C 2: t-BuOK / tetrahydrofuran / 0.75 h / 20 °C 3: AcOH; TFA / tetrahydrofuran / 0.75 h / 25 - 30 °C 4: 8.42 g / aq. NH4OH / tetrahydrofuran / 3 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 58 percent / t-BuMgCl / tetrahydrofuran / 50 °C 2: 62 percent / NH4OAc / propionic acid / 125 °C View Scheme | |
Multi-step reaction with 2 steps 1: 58 percent / t-BuMgCl / tetrahydrofuran / 50 °C 2: 47 percent / NH4OAc / propionic acid / Heating View Scheme |
N-methoxy-N-methyl-6-methylnicotinamide
etoricoxib
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 80 percent / tetrahydrofuran; toluene / 1 h / -10 °C 2: 89 percent / sodium tungstate; aq. H2O2 / aq. H2SO4; methanol / 55 °C 3: t-BuOK / tetrahydrofuran / 0.75 h / 20 °C 4: AcOH; TFA / tetrahydrofuran / 0.75 h / 25 - 30 °C 5: 8.42 g / aq. NH4OH / tetrahydrofuran / 3 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 80 percent / tetrahydrofuran; toluene / 1 h / -10 °C 2: 89 percent / sodium tungstate; aq. H2O2 / aq. H2SO4; methanol / 55 °C 3: 62 percent / NH4OAc / propionic acid / 125 °C View Scheme | |
Multi-step reaction with 3 steps 1: 80 percent / tetrahydrofuran; toluene / 1 h / -10 °C 2: 89 percent / sodium tungstate; aq. H2O2 / aq. H2SO4; methanol / 55 °C 3: 47 percent / NH4OAc / propionic acid / Heating View Scheme |
1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone
etoricoxib
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 89 percent / sodium tungstate; aq. H2O2 / aq. H2SO4; methanol / 55 °C 2: t-BuOK / tetrahydrofuran / 0.75 h / 20 °C 3: AcOH; TFA / tetrahydrofuran / 0.75 h / 25 - 30 °C 4: 8.42 g / aq. NH4OH / tetrahydrofuran / 3 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 89 percent / sodium tungstate; aq. H2O2 / aq. H2SO4; methanol / 55 °C 2: 62 percent / NH4OAc / propionic acid / 125 °C View Scheme | |
Multi-step reaction with 2 steps 1: 89 percent / sodium tungstate; aq. H2O2 / aq. H2SO4; methanol / 55 °C 2: 47 percent / NH4OAc / propionic acid / Heating View Scheme |
1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone
etoricoxib
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: t-BuOK / tetrahydrofuran / 0.75 h / 20 °C 2: AcOH; TFA / tetrahydrofuran / 0.75 h / 25 - 30 °C 3: 8.42 g / aq. NH4OH / tetrahydrofuran / 3 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: t-BuOK / tetrahydrofuran / 0.75 h / 25 °C 2: TFA; AcOH / tetrahydrofuran / 0.75 h / 25 - 30 °C 3: aq. NH3 / tetrahydrofuran / 5 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 30 - 55 °C / Large scale 1.2: Large scale 2.1: sodium hydroxide; water / 25 - 35 °C View Scheme |
etoricoxib
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 46.5 g / isopropyl acetate / 60 - 65 °C 2: t-BuOK / propan-2-ol; tetrahydrofuran / 0.5 h / 25 °C 3: 24.91 g / aq. HCl / 25 - 45 °C 4: t-BuOK / tetrahydrofuran / 0.75 h / 20 °C 5: AcOH; TFA / tetrahydrofuran / 0.75 h / 25 - 30 °C 6: 8.42 g / aq. NH4OH / tetrahydrofuran / 3 h / Heating View Scheme | |
Multi-step reaction with 4 steps 1: 46.5 g / isopropyl acetate / 60 - 65 °C 2: t-BuOK / propan-2-ol; tetrahydrofuran / 0.5 h / 25 °C 3: 24.91 g / aq. HCl / 25 - 45 °C 4: 62 percent / NH4OAc / propionic acid / 125 °C View Scheme | |
Multi-step reaction with 4 steps 1: 46.5 g / isopropyl acetate / 60 - 65 °C 2: t-BuOK / propan-2-ol; tetrahydrofuran / 0.5 h / 25 °C 3: 24.91 g / aq. HCl / 25 - 45 °C 4: 47 percent / NH4OAc / propionic acid / Heating View Scheme |
2-(1-cyclohexenyl)ethylamine
etoricoxib
Conditions | Yield |
---|---|
With C47H70BrO4PPdSi; sodium t-butanolate In tetrahydrofuran at 20℃; for 1h; Schlenk technique; Inert atmosphere; Sealed tube; | 97% |
Molecule structure of Etoricoxib (CAS NO.202409-33-4):
IUPAC Name: 5-Chloro-2-(6-methylpyridin-3-yl)-3-(4-methylsulfonylphenyl)pyridine
Molecular Weight: 358.8419 g/mol
Molecular Formula: C18H15ClN2O2S
Density: 1.298 g/cm3
Melting Point: 134-135 °C
Boiling Point: 510 °C at 760 mmHg
Flash Point: 262.2 °C
Index of Refraction: 1.6
Molar Refractivity: 94.65 cm3
Molar Volume: 276.4 cm3
Surface Tension: 49.6 dyne/cm
Enthalpy of Vaporization: 75.11 kJ/mol
Vapour Pressure: 5.17E-10 mmHg at 25 °C
XLogP3-AA: 3.3
H-Bond Acceptor: 4
Rotatable Bond Count: 3
Exact Mass: 358.054276
MonoIsotopic Mass: 358.054276
Topological Polar Surface Area: 59.9
Heavy Atom Count: 24
Canonical SMILES: CC1=NC=C(C=C1)C2=NC=C(C=C2C3=CC=C(C=C3)S(=O)(=O)C)Cl
InChI: InChI=1S/C18H15ClN2O2S/c1-12-3-4-14(10-20-12)18-17(9-15(19)11-21-18)13-5-7-16(8-6-13)24(2,22)23/h3-11H,1-2H3
InChIKey: MNJVRJDLRVPLFE-UHFFFAOYSA-N
Product Categories: Osteoarthritis and Rheumatoid Arthritis; Intermediates & Fine Chemicals; Pharmaceuticals
Etoricoxib (CAS NO.202409-33-4) is a non-steroidal anti-inflammatory drug (NSAID). It is used for treating the diseases such as rheumatoid arthritis, psoriatic arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout.
Etoricoxib (CAS NO.202409-33-4) is also named as 5-Chloro-6'-methyl-3-(p-(methylsulfonyl)phenyl)-2,3'-bipyridine ; Arcoxia ; Etoxib ; Etropain ; Kingcox ; L-791456 ; MK 0663 ; MK 663 ; Tauxib ; Torcoxia ; UNII-WRX4NFY03R ; 2,3'-Bipyridine, 5-chloro-6'-methyl-3-(4-(methylsulfonyl)phenyl)- . Etoricoxib (CAS NO.202409-33-4) is off-white powder.
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