5-methoxybenzofuran-2-ylboronic acid supplier

Name
5-methoxybenzofuran-2-ylboronic acid
EINECS 1592732-453-0
CAS No. 551001-79-7
Article Data11
CAS DataBase
Density 1.317 g/cm³
Solubility
Melting Point
Formula C₉H₉BO₄
Boiling Point 377.103 °C at 760 mmHg
Molecular Weight 191.979
Flash Point 181.866 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms (5-Methoxy-1-benzofuran-2-yl)boronic acid;5-Methoxybenzofuran-2-ylboronic acid;5-Methoxybenzofuran-2-boronic acid;
PSA 62.83000
LogP 0.12120

Synthetic route

: 13391-28-1
5-methoxybenzofuran

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

Conditions

Conditions	Yield
Stage #1: 5-methoxybenzofuran With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: With Triisopropyl borate In tetrahydrofuran	92%
Stage #1: 5-methoxybenzofuran With n-butyllithium In tetrahydrofuran; hexane at -30℃; for 1.5h; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -30 - 10℃; for 2.17h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water at 10℃;	76%
Stage #1: 5-methoxybenzofuran With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane at 20℃;	37%

: 13391-28-1
5-methoxybenzofuran

: 5419-55-6
Triisopropyl borate

: 7732-18-5
water

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

Conditions

Conditions	Yield
Stage #1: 5-methoxybenzofuran With n-butyllithium In tetrahydrofuran at -60 - -10℃; for 1.25h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran at -60 - 20℃; Stage #3: water With hydrogenchloride In tetrahydrofuran at 20℃; for 1h;	76%

...Expand

: 13391-28-1
5-methoxybenzofuran

: 5419-55-6
Triisopropyl borate

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

Conditions

Conditions	Yield
Stage #1: 5-methoxybenzofuran With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 2h;	69.8%
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere;	37%
Stage #1: 5-methoxybenzofuran With n-butyllithium Stage #2: Triisopropyl borate Stage #3: With hydrogenchloride

: 13391-28-1
5-methoxybenzofuran

: 688-74-4
boric acid tributyl ester

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

Conditions

Conditions	Yield
Stage #1: 5-methoxybenzofuran With n-butyllithium In tetrahydrofuran; hexane at -30℃; for 1h; Stage #2: boric acid tributyl ester In tetrahydrofuran; hexane at 14℃; for 12h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water	48%

: C15H21BO4

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

Conditions

Conditions	Yield
With hydrogenchloride; water In tetrahydrofuran; hexanes

: 13391-28-1
5-methoxybenzofuran

: 1776-66-5
triisopropylborane

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃;

: 69045-79-0
2-choro-5-iodopyridine

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 2‑chloro‑5‑(5‑methoxybenzofuran‑2‑yl)pyridine

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In ethanol for 4h; Suzuki Coupling; Inert atmosphere; Reflux;	91%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In ethanol for 3h; Reflux;	63%

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1268867-67-9
methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

: 1396750-48-3
methyl 3-(isopropyl(methyl)amino)-2-(5-methoxybenzofuran-2-yl)-4a,8a-dihydroquinoxaline-6-carboxylate

Conditions

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 1h; Inert atmosphere;	73%

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 13091-23-1
4-chloro-3-nitropyridine

: 4-(5-methoxy-1-benzofuran-2-yl)-3-nitropyridine

Conditions

Conditions	Yield
Stage #1: (5-methoxy-1-benzofuran-2-yl)boronic acid; 4-chloro-3-nitropyridine With sodium carbonate In 1,4-dioxane for 0.0833333h; Inert atmosphere; Sonication; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 70℃; for 16h; Inert atmosphere;	61%

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1458-01-1
3,5-diamino-6-chloro-pyrazine-2-carboxylic acid methyl ester

: methyl 3,5-diamino-6-(5-methoxybenzofuran-2-yl)pyrazine-2-carboxylate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; toluene Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;	59%

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 4-formyl-2-iodobenzonitrile

: 4-formyl-2-(5-methoxy-1-benzofuran-2-yl)benzonitrile

Conditions

Conditions	Yield
Stage #1: (5-methoxy-1-benzofuran-2-yl)boronic acid; 4-formyl-2-iodobenzonitrile With sodium carbonate In N,N-dimethyl-formamide for 0.0833333h; Inert atmosphere; Sonication; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 70℃; for 16h; Inert atmosphere;	55%

: 5-bromo-2-(difluoromethoxy)-7-methylquinoxaline

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 2-(difluoromethoxy)-5-(5-methoxybenzofuran-2-yl)-7-methylquinoxaline

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In ethanol; dichloromethane; toluene at 100℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Microwave irradiation;	54.8%

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 5-bromo-2-methoxy-7-methylquinoxaline

: 2-methoxy-5-(5-methoxybenzofuran-2-yl)-7-methylquinoxaline

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In ethanol; toluene at 20 - 120℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; Microwave irradiation;	54.1%

: 20511-12-0
2-amino-5-iodopyridine

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1255926-30-7
5-(5-methoxy-1-benzofuran-2-yl)-2-pyridinamine

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water Suzuki coupling; Reflux;	52.1%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water Suzuki coupling; Reflux;	52.1%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water Reflux;	52.1%

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 944401-65-4
5-bromo-6-fluoropyridin-2-ylamine

: 1054629-56-9
6-fluoro-5-(5-methoxy-1-benzofuran-2-yl)pyridin-2-amine

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In ethanol at 140℃; for 0.25h; Suzuki coupling; Microwave irradiation;	50%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In ethanol at 140℃; for 0.25h; Microwave;
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In ethanol

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1120-87-2
4-bromopyridin

: 54402-15-2
4-(5-methoxy-1-benzofuran-2-yl)pyridine

Conditions

Conditions	Yield
Stage #1: (5-methoxy-1-benzofuran-2-yl)boronic acid; 4-bromopyridin With sodium carbonate In N,N-dimethyl-formamide for 0.0833333h; Sonication; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 70℃; for 16h; Inert atmosphere;	42%

: 84539-30-0
5-bromo-N-methylpyridin-2-amine

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1054629-33-2
5-(5-methoxy-1-benzofuran-2-yl)-N-methyl-2-pyridinamine

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In ethanol at 140℃; Suzuki coupling; Microwave irradiation;	37%
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In ethanol at 140℃; for 0.166667h; Microwave;

NaCO3: NaCO3

Pd(PH3)4: Pd(PH3)4

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 619-44-3
methyl 4-iodobenzoate

: 551002-17-6
4-(5-Methoxy-benzofuran-2-yl)-benzoic acid methyl ester

Conditions

Conditions	Yield
In ethanol; toluene	32%

...Expand

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 154237-70-4
4-bromopyridine-3-carbonitrile

: 4-(5-methoxy-1-benzofuran-2-yl)pyridine-3-carbonitrile

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 20 - 90℃; for 7.5h; Inert atmosphere;	8%

: 1532-97-4
4-bromoisoquinoline

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 877263-52-0
C18H13NO2

Conditions

Conditions	Yield
With sodium carbonate; palladium diacetate; triphenylphosphine In 1,2-dimethoxyethane; water Heating / reflux;

: 90145-48-5
5-bromo-2-pyridinecarboxamide

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1054629-20-7
5-(5-Methoxy-benzofuran-2-yl)-pyridine-2-carboxylic acid amide

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In ethanol at 140℃; for 0.166667h; Microwave;
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In ethanol at 140℃; Suzuki coupling; Microwave irradiation;

: 88497-27-2
6-bromopyridazin-3-amine

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1054629-38-7
6-(5-Methoxy-benzofuran-2-yl)-pyridazin-3-ylamine

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In ethanol at 140℃; for 0.166667h; Microwave;

: 13472-79-2
5-iodopyridin-2(1H)-one

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1054629-63-8
5-(5-Methoxy-benzofuran-2-yl)-pyridin-2-ol

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In ethanol at 140℃; for 0.166667h; Microwave;

: 850220-97-2
6-bromo-2-fluoro-pyridin-3-ylamine

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1054629-57-0
2-fluoro-6-(5-methoxy-benzofuran-2-yl)-pyridin-3-ylamine

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In ethanol at 140℃; for 0.166667h; Microwave;
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In ethanol at 140℃; for 0.25h; Suzuki coupling; Microwave irradiation;

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 889676-37-3
6-bromopyridine-3-carboxamide

: 1054629-27-4
6-(5-methoxy-benzofuran-2-yl)-nicotinamide

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In ethanol at 140℃; for 0.166667h; Microwave;
With bis-triphenylphosphine-palladium(II) chloride; triethylamine In ethanol at 140℃; Suzuki coupling; Microwave irradiation;

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1054629-72-9
(5-bromo-3-fluoro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester

: 1054629-73-0
[3-fluoro-5-(5-methoxy-benzofuran-2-yl)-pyridin-2-yl]-methyl-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride In ethanol at 100℃; for 0.5h; Microwave;

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1054629-33-2
5-(5-methoxy-1-benzofuran-2-yl)-N-methyl-2-pyridinamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux 2.1: sodium methylate / methanol / 2 h / Reflux 2.2: 1 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux 2.1: sodium methylate / methanol / 2 h / Reflux 2.2: 1 h / 0 °C / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux 2.1: sodium methylate / methanol / 2 h / Reflux 2.2: 1 h / 0 °C / Reflux View Scheme

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1054629-36-5
2-(6-methylamino-3-pyridinyl)-1-benzofuran-5-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux 2.1: sodium methylate / methanol / 2 h / Reflux 2.2: 1 h / Reflux 3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice 3.2: Cooling with ice View Scheme
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux 2.1: sodium methylate / methanol / 2 h / Reflux 2.2: 1 h / 0 °C / Reflux 3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice 3.2: Cooling with ice View Scheme
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux 2.1: sodium methylate / methanol / 2 h / Reflux 2.2: 1 h / 0 °C / Reflux 3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice View Scheme

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1287783-06-5
tert-butyl 5-(5-(2-(2-(2-methanesulfonylethoxy)ethoxy)ethoxy)-1-benzofuran-2-yl)-2-pyridinyl-N-methylcarbamate

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux 2.1: sodium methylate / methanol / 2 h / Reflux 2.2: 1 h / Reflux 3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice 3.2: Cooling with ice 4.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C 6.1: tetrahydrofuran / Reflux 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C 8.1: triethylamine / dichloromethane / 3 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux 2.1: sodium methylate / methanol / 2 h / Reflux 2.2: 1 h / 0 °C / Reflux 3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice 4.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C 6.1: tetrahydrofuran / Reflux 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C 8.1: triethylamine / dichloromethane / 3 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux
2.1: sodium methylate / methanol / 2 h / Reflux
2.2: 1 h / Reflux
3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice
3.2: Cooling with ice
4.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C
5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C
6.1: tetrahydrofuran / Reflux
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C
8.1: triethylamine / dichloromethane / 3 h / 20 °C
View Scheme

Multi-step reaction with 8 steps
1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux
2.1: sodium methylate / methanol / 2 h / Reflux
2.2: 1 h / 0 °C / Reflux
3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice
4.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C
5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C
6.1: tetrahydrofuran / Reflux
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C
8.1: triethylamine / dichloromethane / 3 h / 20 °C
View Scheme

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1287783-07-6
tert-butyl 5-(5-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)-1-benzofuran-2-yl)-2-pyridinyl-N-methylcarbamate

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux 2.1: sodium methylate / methanol / 2 h / Reflux 2.2: 1 h / Reflux 3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice 3.2: Cooling with ice 4.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C 6.1: tetrahydrofuran / Reflux 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C 8.1: triethylamine / dichloromethane / 3 h / 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / Reflux View Scheme
Multi-step reaction with 9 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux 2.1: sodium methylate / methanol / 2 h / Reflux 2.2: 1 h / 0 °C / Reflux 3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice 4.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C 6.1: tetrahydrofuran / Reflux 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C 8.1: triethylamine / dichloromethane / 3 h / 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / Reflux View Scheme

Yield

Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux
2.1: sodium methylate / methanol / 2 h / Reflux
2.2: 1 h / Reflux
3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice
3.2: Cooling with ice
4.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C
5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C
6.1: tetrahydrofuran / Reflux
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C
8.1: triethylamine / dichloromethane / 3 h / 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / Reflux
View Scheme

Multi-step reaction with 9 steps
1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux
2.1: sodium methylate / methanol / 2 h / Reflux
2.2: 1 h / 0 °C / Reflux
3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice
4.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C
5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C
6.1: tetrahydrofuran / Reflux
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C
8.1: triethylamine / dichloromethane / 3 h / 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / Reflux
View Scheme

: 551001-79-7
(5-methoxy-1-benzofuran-2-yl)boronic acid

: 1287783-08-7
5-(5-(2-(2-(2-fluoro-ethoxy)ethoxy)ethoxy)benzofuran-2-yl)-N-methylpyridin-2-amine

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux 2.1: sodium methylate / methanol / 2 h / Reflux 2.2: 1 h / Reflux 3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice 3.2: Cooling with ice 4.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C 6.1: tetrahydrofuran / Reflux 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C 8.1: triethylamine / dichloromethane / 3 h / 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / Reflux 10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C View Scheme
Multi-step reaction with 10 steps 1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux 2.1: sodium methylate / methanol / 2 h / Reflux 2.2: 1 h / 0 °C / Reflux 3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice 4.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C 5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C 6.1: tetrahydrofuran / Reflux 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C 8.1: triethylamine / dichloromethane / 3 h / 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / Reflux 10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 10 steps
1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux
2.1: sodium methylate / methanol / 2 h / Reflux
2.2: 1 h / Reflux
3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice
3.2: Cooling with ice
4.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C
5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C
6.1: tetrahydrofuran / Reflux
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C
8.1: triethylamine / dichloromethane / 3 h / 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / Reflux
10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
View Scheme

Multi-step reaction with 10 steps
1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / Reflux
2.1: sodium methylate / methanol / 2 h / Reflux
2.2: 1 h / 0 °C / Reflux
3.1: boron tribromide / dichloromethane / 1 h / 20 °C / Cooling with ice
4.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 100 °C
5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C
6.1: tetrahydrofuran / Reflux
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C
8.1: triethylamine / dichloromethane / 3 h / 20 °C
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / Reflux
10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
View Scheme

5-methoxybenzofuran-2-ylboronic acid Specification

The 5-methoxybenzofuran-2-ylboronic acid, with the CAS registry number 551001-79-7, is also known Boronic acid, B-(5-methoxy-2-benzofuranyl)-. This chemical's molecular formula is C₉H₉BO₄ and molecular weight is 191.98. What's more, its systematic name is (5-methoxy-1-benzofuran-2-yl)boronic acid.

Physical properties of 5-methoxybenzofuran-2-ylboronic acid are: (1)ACD/LogP: 1.73; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 1; (5)ACD/BCF (pH 5.5): 14; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 221; (8)ACD/KOC (pH 7.4): 13; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 62.83 Å²; (13)Index of Refraction: 1.597; (14)Molar Refractivity: 49.694 cm³; (15)Molar Volume: 145.785 cm³; (16)Polarizability: 19.7×10^-24cm³; (17)Surface Tension: 51.457 dyne/cm; (18)Density: 1.317 g/cm³; (19)Flash Point: 181.866 °C; (20)Enthalpy of Vaporization: 65.913 kJ/mol; (21)Boiling Point: 377.103 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: OB(O)c1cc2cc(ccc2o1)OC;
(2)InChI: InChI=1S/C9H9BO4/c1-13-7-2-3-8-6(4-7)5-9(14-8)10(11)12/h2-5,11-12H,1H3;
(3)InChIKey: XLIQZZGLIJLKTF-UHFFFAOYSA-N;

Product Name

5-methoxybenzofuran-2-ylboronic acid

Synthetic route

5-methoxybenzofuran-2-ylboronic acid Specification

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