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inquiry5-(prop-1-ynyl)pyridin-3-ylboronic acid CAS:917471-30-8 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high
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inquiry5-(Prop-1-ynyl)pyridine-3-ylboronic acid 917471-30-8 Application:5-(Prop-1-ynyl)pyridine-3-ylboronic acid 917471-30-8
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inquiry5-(prop-1-ynyl)pyridin-3-ylboronic acidAppearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:pharmaceutical intermediate Transportation:by air, by sea, by express
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inquiry917471-30-8 Application:5-(prop-1-ynyl)pyridin-3-ylboronic acid
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inquiry3-bromo-5-(prop-1-yn-1-yl)pyridine
5-(prop-1-ynyl)pyridin-3-ylboronic acid
Conditions | Yield |
---|---|
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane; toluene at -40 - -20℃; for 1.5h; Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexane; toluene | 95% |
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine With n-butyllithium; Triisopropyl borate In 2-methyltetrahydrofuran; toluene at -50℃; for 1.5h; Stage #2: With hydrogenchloride; water In 2-methyltetrahydrofuran; toluene at 20℃; for 0.333333h; Stage #3: With sodium hydroxide In 2-methyltetrahydrofuran; water; toluene | 87% |
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine With n-butyllithium; Triisopropyl borate In 2-methyltetrahydrofuran; toluene at -50℃; for 1.5h; Stage #2: With hydrogenchloride; water In 2-methyltetrahydrofuran; toluene | 87% |
3-bromo-5-(prop-1-yn-1-yl)pyridine
Triisopropyl borate
5-(prop-1-ynyl)pyridin-3-ylboronic acid
Conditions | Yield |
---|---|
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine; Triisopropyl borate With n-butyllithium In 2-methyltetrahydrofuran; toluene at -60℃; for 1.5h; Stage #2: With hydrogenchloride; water In 2-methyltetrahydrofuran; toluene at -50 - 25℃; for 0.333333h; Stage #3: With sodium hydroxide In 2-methyltetrahydrofuran; water; toluene | 87% |
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine; Triisopropyl borate With n-butyllithium In tetrahydrofuran; toluene at -78 - -10℃; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene at 20℃; for 1h; Stage #3: With sodium hydroxide In tetrahydrofuran; water; toluene pH=7 - 8; | 62% |
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine; Triisopropyl borate With n-butyllithium In tetrahydrofuran; hexane; toluene at -40 - -20℃; for 0.75h; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water; toluene Stage #3: With sodium hydroxide In tetrahydrofuran; hexane; water; toluene pH=7; | |
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine; Triisopropyl borate With n-butyllithium In tetrahydrofuran; hexane; toluene at -40 - -20℃; for 0.75h; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; toluene |
3,5-dibromopyridine
5-(prop-1-ynyl)pyridin-3-ylboronic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: triethylamine; tetrabutyl ammonium fluoride / tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / toluene; tetrahydrofuran / 20 °C / Inert atmosphere 2.1: n-butyllithium; Triisopropyl borate / toluene; tetrahydrofuran / 1.42 h / -78 - 20 °C / Inert atmosphere 2.2: 1 h / 20 °C 2.3: pH 7 - 8 View Scheme | |
Multi-step reaction with 2 steps 1.1: triethylamine; tetrabutyl ammonium fluoride; copper(l) iodide / tetrakis(triphenylphosphine) palladium(0) / toluene; tetrahydrofuran / 20 °C / Inert atmosphere 2.1: n-butyllithium / toluene; tetrahydrofuran / -78 - -10 °C / Inert atmosphere 2.2: 1 h / 20 °C 2.3: pH 7 - 8 View Scheme | |
Multi-step reaction with 2 steps 1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride; triethylamine / toluene / 20 °C 2: n-butyllithium; Triisopropyl borate; ammonium carbonate / tetrahydrofuran; water; toluene / -40 - -10 °C View Scheme |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
(R)-5-(3-amino-1-(3-bromophenyl)-4-fluoro-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
(R)-5-(3-Amino-4-fluoro-1-(3-(5-(prop-1-ynyl)pyridin-3-yl)phenyl)-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
Conditions | Yield |
---|---|
With potassium carbonate; sodium tetrachloropalladate(II); 3-(di-tert-butylphosphino)-propane-1-sulfonic acid In 2-methyltetrahydrofuran; water for 2h; Product distribution / selectivity; Reflux; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; tert-butyl alcohol at 60℃; for 1h; | 90% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
Conditions | Yield |
---|---|
With potassium phosphate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) In 1,4-dioxane; water at 100℃; for 0.5h; Microwave irradiation; | 74% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
5-(3-Amino-1-(2-bromopyridin-4-yl)-4-fluoro-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
5-(3-Amino-4-fluoro-1-(5'-(prop-1-ynyl)-2,3'-bipyridin-4-yl)-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
Conditions | Yield |
---|---|
With potassium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In 1,4-dioxane; water at 100℃; for 0.25h; Product distribution / selectivity; Microwave irradiation; | 68% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
(S)-tert-butyl-(4-(5-bromo-2-chlorothiophen-3-yl)-1,4-dimethyl-6-oxotetrahydropyrimidin-2(1H)-ylidene) carbamate
(S)-tert-butyl (4-(2-chloro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)thiophen-3-yl)-1,4-dimethyl-6-oxotetrahydropyrimidin-2(1H)-ylidene)carbamate
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In dichloromethane; tert-butyl alcohol at 65℃; for 3h; | 67% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
(1r,4r)-6'-bromo-4-methoxy-4,5''-dimethyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine
(1r,4r)-4-methoxy-4,5''-dimethyl-6'-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine
Conditions | Yield |
---|---|
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 130℃; for 0.333333h; | 58% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
(1r,4r)-4"-amino-6'-bromo-5"-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2"-imidazol]-4-ol
(1r,4r)-4"-amino-5"-methyl-6'-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3'H-dispiro[cyclohexane-1,2'-indene-1',2"-imidazol]-4-ol
Conditions | Yield |
---|---|
With sodium tetrachloropalladate(II); 3-(di-tert-butylphosphino)-propane-1-sulfonic acid; potassium carbonate In 2-methyltetrahydrofuran; water at 120℃; for 0.666667h; Inert atmosphere; Microwave irradiation; | 55% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
(4S,6S)-4-(5-bromo-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine
(4S,6S)-4-(2-fluoro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)phenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine
Conditions | Yield |
---|---|
In 1,4-dioxane; water; ethyl acetate | 55% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
(1r,1'R,4R)-6'-bromo-4-methoxy-5''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazole]-4"-amine
(1r,1’R,4R)-4-methoxy-5”-methyl-6’-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3’H-dispiro[cyclohexane-1,2’-indene-1’2”-imidazol]-4”-amine
Conditions | Yield |
---|---|
With potassium carbonate; sodium tetrachloropalladate(II); 3-(di-tert-butylphosphino)-propane-1-sulfonic acid In 2-methyltetrahydrofuran; water at 80℃; Inert atmosphere; | 43% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
5'-bromo-4-methoxy-5"-methyldispiro[cyclohexane-1,2'-[1]benzofuran-3',2"-imidazol]-4"-amine
4-methoxy-5"-methyl-5'-[5-(prop-1-yn-1-yl)pyridin-3-yl]dispiro[cyclohexane-1,2'-[1]benzofuran-3',2"-imidazol]-4"-amine
Conditions | Yield |
---|---|
With caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; ethanol; water | 42% |
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 65℃; Suzuki coupling; | 39% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
(1r,4r)-6'-bromo-4-methoxy-5''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazole]-4"-amine
(1r,4r)-4-methoxy-5''-methyl-6'-(5-prop-1-yn-1-ylpyridin-3-yl)-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine
Conditions | Yield |
---|---|
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 2-methyltetrahydrofuran; water at 100℃; for 1h; Product distribution / selectivity; Microwave irradiation; | 36% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
(R)-5-(3-bromophenyl)-5-(4-methoxy-3,5-dimethylphenyl)-5H-pyrrolo[3,4-b]pyrazin-7-amine
(S)-5-(4-methoxy-3,5-dimethylphenyl)-5-(3-(5-(prop-1-ynyl)pyridin-3-yl)phenyl)-5H-pyrrolo[3,4-b]pyrazin-7-amine
Conditions | Yield |
---|---|
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 90℃; for 4h; Inert atmosphere; | 34% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
tert-butyl ((4aR,7aR)-7a-(5-bromo-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate
Conditions | Yield |
---|---|
With tert.-butyl lithium; bis-triphenylphosphine-palladium(II) chloride In 1,2-dimethoxyethane; ethanol; water at 90℃; for 0.0833333h; | 33.7% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
tert-butyl ((4S,6S)-4-(5-bromo-3-chlorothiophen-2-yl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate
tert-butyl ((4S,6S)-4-(3-chloro-5-(5-(prop-1-ynyl)pyridin-3-yl)thiophen-2-yl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In ethanol; water; N,N-dimethyl-formamide at 90℃; for 1h; | 33.3% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
(S)-tert-butyl (5-(5-bromo-3-chlorothiophen-2-yl)-2,5-dimethyl-1,1-dioxido-1,2,4-thiadiazinan-3-ylidene)carbamate
Conditions | Yield |
---|---|
Stage #1: 5-(prop-1-ynyl)pyridin-3-ylboronic acid; (S)-tert-butyl (5-(5-bromo-3-chlorothiophen-2-yl)-2,5-dimethyl-1,1-dioxido-1,2,4-thiadiazinan-3-ylidene)carbamate With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In water; tert-butyl alcohol at 65℃; Suzuki Coupling; Inert atmosphere; Stage #2: With di-tert-butyl dicarbonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; | 26% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
6‘-bromo-4"-fluoro-4-methoxy-3‘H-dispiro[cyclohexane-1,2’-indene-1‘,2"-pyrrol]-5"-amine
A
(1r,4r)-4’‘-fluoro-4-methoxy-6’-(5-(prop-1-yn-1-yl)pyridin-3-yl)-3‘H-dispiro[cyclohexane-1,2‘-indene-1,2’‘-pyrrol]-5”-amine
B
(1s,4s)-4’‘-fluoro-4-methoxy-6’-(5-(prop-1-yn-1-yl)pyridin-3-yl)-3‘H-dispiro[cyclohexane-1,2‘-indene-1,2’‘-pyrrol]-5”-amine
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 2h; Suzuki Coupling; | A 22% B 11% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
Conditions | Yield |
---|---|
With sodium tetrachloropalladate(II); 3-(di-tert-butylphosphino)-propane-1-sulfonic acid; potassium carbonate In 2-methyltetrahydrofuran; water at 90℃; for 0.5h; Inert atmosphere; Sealed tube; | 16% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
(R)-5-(3-Amino-1-(3-bromophenyl)-4-fluoro-1H-isoindol-1-yl)-1,3-dimethylpyridin-2(1H)-one
5-(3-Amino-4-fluoro-1-(3-(5-(prop-1-ynyl)pyridin-3-yl)phenyl)-1H-isoindol-1-yl)-1,3-dimethylpyridin-2(1H)-one
Conditions | Yield |
---|---|
With potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 130℃; for 0.25h; Microwave irradiation; | 14% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
5-(3-Amino-1-(2-bromopyridin-4-yl)-4-fluoro-1H-isoindol-1-yl)-1,3-diethylpyridin-2(1H)-one
5-(3-Amino-4-fluoro-1-(5'-(prop-1-ynyl)-2,3'-bipyridin-4-yl)-1H-isoindol-1-yl)-1,3-diethylpyridin-2(1H)-one
Conditions | Yield |
---|---|
With caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; ethanol; water at 150℃; for 0.5h; Microwave irradiation; | 10% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
A
(1s,4r)-4-methoxy-5''-methyl-7'-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3',4'-dihydrodispiro[cyclohexane-1,2'-naphthalene-1',2''-imidazol]-4''-amine
B
(1r,4s)-4-methoxy-5''-methyl-7'-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3',4'-dihydrodispiro[cyclohexane-1,2'-naphthalene-1',2''-imidazol]-4''-amine
Conditions | Yield |
---|---|
With sodium tetrachloropalladate(II); 3-(di-tert-butylphosphino)-propane-1-sulfonic acid; potassium carbonate In 2-methyltetrahydrofuran; water at 100℃; Inert atmosphere; Sealed tube; Microwave irradiation; | A 4% B 5% |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
(S)-tert-butyl (4-(4-bromothiophen-2-yl)-1,4-dimethyl-6-oxotetrahydropyrimidin-2(1H)-ylidene)carbamate
C23H26N4O3S
Conditions | Yield |
---|---|
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tert-butyl alcohol at 65℃; for 0.75h; |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
(R)-4-(3-bromothiophen-2-yl)-2-tert-butyloxycarbamimino-1,4-dimethyl-6-oxo-1,3,8-diazaspiro[5.5]decane-8-methyl
Conditions | Yield |
---|---|
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; tert-butyl alcohol at 110℃; for 0.25h; Suzuki Coupling; Microwave irradiation; |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
5-(3-Amino-1-(2-bromopyridin-4-yl)-4-fluoro-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
A
(R)-5-(3-amino-4-fluoro-1-(5'-(prop-1-ynyl)-2,3'-bipyridin-4-yl)-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
B
(S)-5-(3-amino-4-fluoro-1-(5'-(prop-1-ynyl)-2,3'-bipyridin-4-yl)-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / 1,4-dioxane; water / 0.25 h / 100 °C / Microwave irradiation 2: Chiralpak AD-H column / isopropyl alcohol; diethylamine; carbon dioxide / Resolution of racemate; Supercritical fluid View Scheme |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
(1r,1’R,4R)-4-methoxy-5”-methyl-6’-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3’H-dispiro[cyclohexane-1,2’-indene-1’2”-imidazol]-4”-amine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 2-methyltetrahydrofuran / 1 h / 100 °C / Microwave irradiation 2: ethanol / 18.5 h / 20 - 55 °C 3: sodium hydroxide / dichloromethane; water / 0.25 h / 25 °C View Scheme |
5-(prop-1-ynyl)pyridin-3-ylboronic acid
A
(1r,1'S,4S)-4-methoxy-5''-methyl-6'-(5-prop-1-yn-1-ylpyridin-3-yl)-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine
B
(1r,1’R,4R)-4-methoxy-5”-methyl-6’-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3’H-dispiro[cyclohexane-1,2’-indene-1’2”-imidazol]-4”-amine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 2-methyltetrahydrofuran / 1 h / 100 °C / Microwave irradiation 2: diethylamine / carbon dioxide; methanol View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 2-methyltetrahydrofuran / 1 h / 100 °C / Microwave irradiation 2: ethanol / 18.5 h / 20 - 55 °C View Scheme |
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