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Conditions | Yield |
---|---|
With copper(II) oxide at 180℃; | 75% |
With copper(II) oxide |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; hydrogen isocyanide In N,N-dimethyl-aniline; 1,2-dichloro-benzene |
Conditions | Yield |
---|---|
With N,N-diethylaniline | |
With hydrogenchloride; hydrogen isocyanide In N,N-dimethyl-aniline; nitrobenzene; cyclohexanol |
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen isocyanide In dichloromethane; N,N-dimethyl-aniline |
Conditions | Yield |
---|---|
With N,N-diethylaniline | |
With 1-methyl-pyrrolidin-2-one; N,N-diethylaniline |
4-methyloxazole
4-methylphenyl methylsulfide
4-methyl-2-(p-tolyl)oxazole
Conditions | Yield |
---|---|
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride; 2,2,6,6-tetramethylpiperidyl zinc chloride-lithium chloride complex In tetrahydrofuran at 80℃; for 6h; Inert atmosphere; regioselective reaction; | 98% |
4-methyloxazole
triisopropylsilyl trifluoromethanesulfonate
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran; hexane at -30℃; for 0.5h; Stage #2: triisopropylsilyl trifluoromethanesulfonate In tetrahydrofuran; hexane at -10℃; | 98% |
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: triisopropylsilyl trifluoromethanesulfonate In tetrahydrofuran at -10 - 25℃; for 12h; Inert atmosphere; | 81% |
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #3: C14H15BrN6O4 With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; hexane at 75℃; for 0.166667h; Negishi coupling reaction; Inert atmosphere; Microwave irradiation; | 88% |
4-methyloxazole
3-<1-(Methoxycarbonyl)cyclopropyl>-2-propinsaeure-methylester
4-<1-(Methoxycarbonyl)cyclopropyl>-3-furancarbonsaeure-methylester
Conditions | Yield |
---|---|
at 220℃; for 20h; | 87% |
4-methyloxazole
chloro-trimethyl-silane
(Z)-2-isocyano-O-(trimethylsilyl)-1-propen-1-ol
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether at -78℃; | 85% |
With n-butyllithium 1.) hexane, Et2O, 1 h; Yield given. Multistep reaction; |
4-methyloxazole
(2-amino-6-bromo-3-nitropyridin-4-yl)-(6-methylpyridin-3-ylmethyl)carbamic acid ethyl ester
[2-amino-6-(4-methyloxazol-2-yl)-3-nitropyridin-4-yl]-(6-methylpyridin-3-ylmethyl)carbamic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #3: (2-amino-6-bromo-3-nitropyridin-4-yl)-(6-methylpyridin-3-ylmethyl)carbamic acid ethyl ester With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; hexane at 60℃; for 0.25h; Negishi coupling reaction; Inert atmosphere; Microwave irradiation; | 85% |
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Cooling with acetone-dry ice; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -78 - 20℃; for 0.25h; Stage #3: (2-amino-6-bromo-3-nitropyridin-4-yl)-(6-methylpyridin-3-ylmethyl)carbamic acid ethyl ester; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; hexane at 60℃; for 0.25h; Microwave irradiation; |
4-methyloxazole
methyl 3-<1'-chlorocyclopropyl>propiolate
A
4-(1-Chlorcyclopropyl)-3-furancarbonsaeure-methylester
B
acetonitrile
Conditions | Yield |
---|---|
at 140℃; | A 80% B n/a |
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether at -78℃; | 80% |
With n-butyllithium 1.) hexane, Et2O, 1 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #3: C15H16BrN5O5 With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; hexane at 90℃; for 0.0833333h; Negishi coupling reaction; Inert atmosphere; Microwave irradiation; | 80% |
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #3: C14H15BrN6O4 With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; hexane at 65℃; for 1h; Negishi coupling reaction; Inert atmosphere; | 75% |
4-methyloxazole
4-bromo-2-methylpyridine
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium; zinc(II) chloride In tetrahydrofuran; 2-methyltetrahydrofuran at -78 - 22℃; for 0.5h; Stage #2: 4-bromo-2-methylpyridine With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; 2-methyltetrahydrofuran at 60℃; for 2h; | 70% |
4-methyloxazole
3,3,3-trifluoroprop-1-yne
A
3-trifluoromethyl furan
B
acetonitrile
Conditions | Yield |
---|---|
In toluene at 180 - 190℃; for 13h; | A 67% B 6% |
4-methyloxazole
(2-amino-6-bromo-3-nitro-pyridin-4-yl)-(3-cyano-benzyl)-carbamic acid ethyl ester
[2-amino-6-(4-methyl-oxazol-2-yl)-3-nitro-pyridin-4-yl]-(3-cyano-benzyl)-carbamic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #3: (2-amino-6-bromo-3-nitro-pyridin-4-yl)-(3-cyano-benzyl)-carbamic acid ethyl ester With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; hexane at 60℃; for 0.25h; Negishi coupling reaction; Inert atmosphere; Microwave irradiation; | 65% |
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran; diethyl ether at -78℃; for 1h; Stage #2: tributyltin chloride In tetrahydrofuran; diethyl ether at -78℃; for 1h; | 61% |
Stage #1: 4-methyloxazole In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: tributyltin chloride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; |
4-methyloxazole
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Stage #2: With 1,2-dibromo-1,1,2,2-tetrafluoroethane In tetrahydrofuran; hexane at -78 - 25℃; regioselective reaction; | 61% |
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium; zinc(II) chloride In tetrahydrofuran; 2-methyltetrahydrofuran at -78 - 22℃; for 0.5h; Stage #2: 5-bromo-2-methylpyridine With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; 2-methyltetrahydrofuran at 60℃; for 2h; | 53% |
4-methyloxazole
5-bromo-2-(cyanomethyl)benzonitrile
Conditions | Yield |
---|---|
With potassium acetate; palladium diacetate In N,N-dimethyl-formamide at 90℃; for 3h; Inert atmosphere; | 50% |
4-methyloxazole
3-Cyclopropyl-2-propinsaeure-methylester
4-Cyclopropyl-3-furancarbonsaeure-methylester
Conditions | Yield |
---|---|
In toluene at 220 - 230℃; for 16h; | 45% |
4-methyloxazole
methyl 2-bromoisonicotinate
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: With zinc(II) chloride In tetrahydrofuran at -78 - 20℃; Stage #3: methyl 2-bromoisonicotinate With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 60℃; for 0.5h; Inert atmosphere; Microwave irradiation; | 45% |
4-methyloxazole
(2-amino-6-bromo-3-nitro-pyridin-4-yl)-(6-trifluoromethyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester
[2-amino-6-(4-methyl-oxazol-2-yl)-3-nitro-pyridin-4-yl]-(6-trifluoromethyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #3: (2-amino-6-bromo-3-nitro-pyridin-4-yl)-(6-trifluoromethyl-pyridin-3-ylmethyl)-carbamic acid ethyl ester With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; hexane at 90℃; for 0.0833333h; Negishi coupling reaction; Inert atmosphere; Microwave irradiation; | 44% |
4-methyloxazole
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether; hexane at -70 - 20℃; for 2h; Inert atmosphere; | 40% |
With n-butyllithium 1.) THF, -75 deg C, 45 min, 2.) THF, from -75 deg C to RT; Yield given. Multistep reaction; | |
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.75h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; |
4-methyloxazole
8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine
Conditions | Yield |
---|---|
With caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine In N,N-dimethyl-formamide at 130℃; | 39% |
4-methyloxazole
methyl 3-<1'-chlorocyclopropyl>propiolate
4-(1-Chlorcyclopropyl)-3-furancarbonsaeure-methylester
Conditions | Yield |
---|---|
In toluene at 150℃; for 18h; | 30% |
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether at -78℃; | 30% |
With n-butyllithium 1.) hexane, Et2O, 1 h; Yield given. Multistep reaction; |
4-methyloxazole
1,5-dihydro-3-(4,7-dihydro-1,3-dioxepin-2-yl)-9-hydroxy-8-methyl-3H-<1,3>dioxepino<5,6-c>pyridine
Conditions | Yield |
---|---|
With perchloric acid for 4h; Heating; | 27.7% |
4-methyloxazole
4,7-dihydro-2-<3-(4,7-dihydro-1,3-dioxepin-2-yl)-propyl>-1,3-dioxepin
A
7-[3-(4,7-Dihydro-[1,3]dioxepin-2-yl)-propyl]-3-methyl-5,9-dihydro-6,8-dioxa-2-aza-benzocyclohepten-4-ol
Conditions | Yield |
---|---|
With acetic anhydride; nitrobenzene; hydroquinone at 180 - 190℃; for 2h; | A 23.6% B 11.9% |
4-methyloxazole
6-chloro-4-iodo-1-(phenylsulfonyl)-1H-indazole
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.5h; Stage #2: 6-chloro-4-iodo-1-(phenylsulfonyl)-1H-indazole With tetrakis(triphenylphosphine) palladium(0); zinc(II) chloride In tetrahydrofuran; hexane at 0℃; for 7h; Reflux; | 22% |
4-methyloxazole
2-bromopentan-3-one
A
2-(2,2,3,3-Tetrafluorpropoxy)-3-pentanon
endo-2,endo-4,7-Trimethyl-8-oxa-6-azabicyclo<3.2.1>oct-6-en-3-on
Conditions | Yield |
---|---|
With 2,2,3,3-tetrafluoropropanol; sodium 2,2,3,3-tetrafluoropropan-1-olate for 19h; | A 12% B 13% |
4-methyloxazole
chloroformic acid ethyl ester
methyl 4-methyloxazole-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: 4-methyloxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: chloroformic acid ethyl ester In tetrahydrofuran; hexane at -78 - 20℃; | 13% |
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