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CAS No.: | 221615-72-1 |
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Name: | 1-(6-Methylpyridin-3-yl)-2-(4-(Methylthio)phenyl)ethanone |
Article Data: | 11 |
Molecular Structure: | |
Formula: | C15H15NOS |
Molecular Weight: | 257.356 |
Synonyms: | Etoricoxib Intermediate 1;1-(6-Methylpyridin-3-yl)-2-(4-(Methylthio)phenyl)ethanone;1-(6-Methyl-3-pyridinyl)-2-[4-(Methylthio)phenyl]-ethanone;1-(6-Methylpyridin-3-yl)-2-(4-(methylthio)phenyl)ethan-1-one;1-(6-Methyl-3-pyridinyl)-2-[4-(methylsulfanyl)phenyl]ethanone;1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone;Ethanone, 1-?(6-?methyl-?3-?pyridinyl)?-?2-?[4-?(methylthio)?phenyl]?-;Etoricoxib impurity 14/1-(6-Methylpyridin-3-yl)-2-[4-(methylthio)phenyl]ethanone |
EINECS: | 807-172-3 |
Density: | 1.17±0.1 g/cm3(Predicted) |
Melting Point: | 111-113℃ |
Boiling Point: | 426.7±40.0 °C(Predicted) |
PSA: | 55.26000 |
LogP: | 3.53730 |
Methyl 6-methylnicotinate
1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone
Conditions | Yield |
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With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1h; Reagent/catalyst; Temperature; | 87.7% |
N-methoxy-N-methyl-6-methylnicotinamide
1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone
Conditions | Yield |
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In tetrahydrofuran; toluene at -10℃; for 1h; | 80% |
Methyl 6-methylnicotinate
1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone
Conditions | Yield |
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With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1h; | 78.5% |
1-(chloromethyl)-4-methylthiobenzene
N-methoxy-N-methyl-6-methylnicotinamide
1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone
Conditions | Yield |
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Stage #1: 1-(chloromethyl)-4-methylthiobenzene With magnesium In tetrahydrofuran; toluene for 3 - 4h; Stage #2: N-methoxy-N-methyl-6-methylnicotinamide In toluene at -20℃; for 1.5h; | 76% |
With magnesium; ethylene dibromide In tetrahydrofuran; toluene at 36℃; | 62% |
Methyl 6-methylnicotinate
2-(4-(methylthio)phenyl)acetic acid
1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone
Conditions | Yield |
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With tert-butylmagnesium chloride In tetrahydrofuran at 65 - 70℃; for 1h; | 72% |
Stage #1: 2-(4-(methylthio)phenyl)acetic acid With tert-butylmagnesium chloride In tetrahydrofuran at 60℃; for 1h; Flow reactor; Stage #2: Methyl 6-methylnicotinate In tetrahydrofuran at 60℃; for 1h; Flow reactor; Stage #3: With hydrogenchloride In water; toluene Temperature; Flow reactor; |
1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone
Conditions | Yield |
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In tetrahydrofuran; toluene at -20 - -10℃; for 1h; Temperature; Inert atmosphere; | 60% |
Methyl 6-methylnicotinate
1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone
Conditions | Yield |
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Multi-step reaction with 2 steps 1: i-PrMgCl / toluene; tetrahydrofuran / 0.5 h / -10 °C 2: 80 percent / tetrahydrofuran; toluene / 1 h / -10 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: toluene / 0.67 h / Reflux 1.2: Reflux 2.1: hydrogenchloride; water; acetic acid / 40 °C / Reflux 2.2: 0.17 h / 0 - 5 °C / pH 7 - 7.2 View Scheme | |
Multi-step reaction with 2 steps 1: sodium methylate / toluene / 0.67 h / 25 - 30 °C / pH 5.2-6.2 / Reflux 2: hydrogenchloride / toluene; water; acetic acid / 20 °C / pH 6.9-7.1 View Scheme | |
Multi-step reaction with 2 steps 1: isopropylmagnesium chloride / toluene; tetrahydrofuran / 0.5 h / -20 - -10 °C / Inert atmosphere 2: toluene; tetrahydrofuran / 1 h / -20 - -10 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: isopropylmagnesium chloride / toluene; tetrahydrofuran / 0.5 h / -20 - -10 °C / Inert atmosphere 2: diethyl ether / -10 - 0 °C View Scheme |
2-[4-(methylsulfanyl)phenyl]acetonitrile
1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: toluene / 0.67 h / Reflux 1.2: Reflux 2.1: hydrogenchloride; water; acetic acid / 40 °C / Reflux 2.2: 0.17 h / 0 - 5 °C / pH 7 - 7.2 View Scheme | |
Multi-step reaction with 2 steps 1: sodium methylate / toluene / 0.67 h / 25 - 30 °C / pH 5.2-6.2 / Reflux 2: hydrogenchloride / toluene; water; acetic acid / 20 °C / pH 6.9-7.1 View Scheme |
1-(6-methyl-3-pyridinyl)-2-cyano-2-[(4-methylthio)phenyl]ethanone
1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone
Conditions | Yield |
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Stage #1: 1-(6-methyl-3-pyridinyl)-2-cyano-2-[(4-methylthio)phenyl]ethanone With hydrogenchloride; water; acetic acid at 40℃; Reflux; Stage #2: With ammonia In water at 0 - 5℃; for 0.166667h; pH=7 - 7.2; Product distribution / selectivity; | |
With hydrogenchloride In water; acetic acid; toluene at 20℃; pH=6.9-7.1; Concentration; Reagent/catalyst; Solvent; Time; Temperature; | 5.2 g |
Methyl 6-methylnicotinate
2-[4-(methylsulfanyl)phenyl]acetonitrile
1-(6-methyl-3-pyridinyl)-2-[4-(methyl sulfide)phenyl]ethanone
Conditions | Yield |
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Stage #1: Methyl 6-methylnicotinate; 2-[4-(methylsulfanyl)phenyl]acetonitrile With hydrogenchloride; sodium methylate In water; toluene at 25 - 30℃; pH=5.2-6.2; Reflux; Stage #2: With hydrogenchloride In water; acetic acid; toluene at 40 - 50℃; Reflux; |