937366-54-6

Basic information

• Product Name: PINACOL ESTER INDOLE-5-BORONIC ACID
• Synonyms: PINACOL ESTER INDOLE-5-BORONIC ACID;Indole-3-boronic acid pinacol ester;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;3-Indoleboronic Acid Pinacol Ester
• CAS NO: 937366-54-6
• Molecular Formula: C₁₄H₁₈BNO₂
• Molecular Weight: 243.10922
• Mol File: 937366-54-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 396.0±15.0 °C(Predicted)
• Appearance: /
• Density: 1.11
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 17.01±0.30(Predicted)
• CAS DataBase Reference: PINACOL ESTER INDOLE-5-BORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: PINACOL ESTER INDOLE-5-BORONIC ACID(937366-54-6)
• EPA Substance Registry System: PINACOL ESTER INDOLE-5-BORONIC ACID(937366-54-6)

Safety Data

• Hazardous Substances Data: 937366-54-6(Hazardous Substances Data)

Usage

General Description

PINACOL ESTER INDOLE-5-BORONIC ACID is a chemical compound composed of an indole moiety and a boronic acid functional group. It is commonly used in organic synthesis as a building block to create more complex molecules. The PINACOL ESTER group provides a convenient handle for further manipulation, while the boron atom enables cross-coupling reactions with various electrophiles. PINACOL ESTER INDOLE-5-BORONIC ACID is frequently utilized in medicinal chemistry and pharmaceutical research for the design and synthesis of potential drug candidates. Additionally, it has shown promising potential as a versatile tool in the development of new materials and chemical processes.

InChI:InChI=1S/C14H18BNO2/c1-13(2)14(3,4)18-15(17-13)11-9-16-12-8-6-5-7-10(11)12/h5-9,16H,1-4H3

Synthetic route

indole (120-72-9) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 4h; Solvent; Temperature; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	78%

3-bromoindole (1484-27-1) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
Stage #1: 3-bromoindole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at 20℃; for 5h;	70%

tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (942070-45-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
at 180℃; for 0.75h;	64%

indole (120-72-9) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
Stage #1: indole; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With triethylamine In tetrahydrofuran at 80℃; for 0.333333h; Schlenk technique; Inert atmosphere; Stage #2: With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin at 80℃; for 4h; Schlenk technique; Inert atmosphere;	50%
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	7 %Chromat.

3‑(4,4,5,5‑tetramethyl‑1,3,2‑dioxaborolan‑2‑yl)‑1‑(triisopropylsilyl)‑1H‑indole (476004-82-7) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
With tetrabutyl ammonium fluoride

1-(triisopropylsilyl)-1H-indole (123191-00-4) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / 1/2[IrCl(COD)]2-(4,4'-di-tert-butyl-2,2'-bipyridine) / octane / 16 h / 80 °C 2: TBAF View Scheme

bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / 1/2[IrCl(COD)]2-(4,4'-di-tert-butyl-2,2'-bipyridine) / octane / 16 h / 80 °C 2: TBAF View Scheme
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 0.33 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox View Scheme
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 2 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox View Scheme

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere; Glovebox 2: methanol / tetrahydrofuran / 20 °C / Inert atmosphere; Glovebox View Scheme

indole (120-72-9) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / benzene-d6 / 0.5 h / 80 °C / Inert atmosphere; Glovebox; Sealed tube 2: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere; Glovebox 3: methanol / tetrahydrofuran / 20 °C / Inert atmosphere; Glovebox View Scheme
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / dichloromethane / 5 h / 0 - 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 0.33 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox View Scheme
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 0.33 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox View Scheme
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 2 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox View Scheme

1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
With methanol In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox;	139 mg
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In hexane at 60℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	94 %Chromat.

indole (120-72-9) + bis(pinacol)diborane (73183-34-3) → 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole + 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 0.166667h; Time; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	A 36 %Chromat. B 15 %Chromat. C 27 %Chromat.
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 0.333333h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	A 24 %Chromat. B 22 %Chromat. C 32 %Chromat.
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 1h; Time; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	A 6 %Chromat. B 25 %Chromat. C 51 %Chromat.

indole (120-72-9) + bis(pinacol)diborane (73183-34-3) → 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 2h; Time; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	A 12 %Chromat. B 72 %Chromat.

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	91 %Chromat.

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Conditions	Yield
With triethylamine In tetrahydrofuran at 80℃; for 1h; Inert atmosphere; Sealed tube; Glovebox;	95%

3-bromo-(1-tert-butyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (862728-61-8) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 1-(tert-butyl)-3-(1H-indol-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 150℃; for 0.25h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Microwave irradiation;	70%

1,4-dibromo-2-nitrobenzene (3460-18-2) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-(4-bromo-2-nitrophenyl)-1H-indole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate In ethanol; water; toluene at 80℃; for 16h;	60%

2-nitrophenyl bromide (577-19-5) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-(2-nitrophenyl)-1H-indole (56366-31-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate In ethanol; water; toluene at 80℃; for 16h;	60%

4-(4-chloro-6-methoxy-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole + trifluoroacetic acid (76-05-1) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → (x)C2HF3O2*C24H18FN5O2

Conditions	Yield
Stage #1: 4-(4-chloro-6-methoxy-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole; 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 20℃; for 14h; Suzuki Coupling; Reflux; Stage #2: trifluoroacetic acid In 1,2-dimethoxyethane; water for 0.25h;	44%

3-bromo-4-methoxy-6-methyl-2H-pyran-2-one (670-35-9) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-(1H-indol-3-yl)-4-methoxy-6-methyl-2H-pyran-2-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 24h; Suzuki Coupling;	42%

3-bromo-4-methoxy-6-methyl-2H-pyran-2-one (670-35-9) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-(1H-indol-2-yl)-4-methoxy-6-methyl-2H-pyran-2-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 24h; Suzuki Coupling;	41%

3-bromo-4,6-dimethyl-2H-pyran-2-one (669-95-4) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-(1H-indol-3-yl)-4,6-dimethyl-2H-pyran-2-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 24h; Suzuki Coupling;	38%

2,4,5-trichloropyrimidine (5750-76-5) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-(2,5-dichloropyrimidine-4-yl)-1H-indole (937366-57-9)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C22H22ClN5

Conditions	Yield
Multi-step reaction with 2 steps 1: Pd(PPh3)4 / 1,2-dimethoxy-ethane 2: 2-methoxy-ethanol View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C25H27ClN6

Conditions	Yield
Multi-step reaction with 2 steps 1: Pd(PPh3)4 / 1,2-dimethoxy-ethane 2: 2-methoxy-ethanol View Scheme

N-[4-(2-bromothiazol-4-yl)-3-chlorophenyl]-1,1,1-trifluoro-methanesulfonamide + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → N-{3-chloro-4-[2-(1H-indol-3-yl)-1,3-thiazol-4-yl]phenyl}-1,1,1-trifluoromethanesulfonamide

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 18h; Inert atmosphere;	42 mg
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 18h; Inert atmosphere;	43 mg
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 18h; Inert atmosphere;	42 mg

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-bromo-5,6-dihydroindolo[2,3-b]indole

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C26H17BrN2

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C View Scheme
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 4: N-Bromosuccinimide / dichloromethane / 5 h / 0 - 20 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → indolo[2,3-b]indole

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 5,6-diphenyl-5,6-dihydroindolo[2,3-b]indole

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C26H16F2N2

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C26H15BrF2N2

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 4: N-Bromosuccinimide / dichloromethane / 5 h / 0 - 20 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C44H31N3

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 4: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate / toluene / 3 h / 80 °C View Scheme
Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 4: N-Bromosuccinimide / dichloromethane / 5 h / 0 - 20 °C 5: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate / toluene / 3 h / 80 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C44H29F2N3

Conditions

Yield

Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 4: N-Bromosuccinimide / dichloromethane / 5 h / 0 - 20 °C 5: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate / toluene / 3 h / 80 °C View Scheme

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 120-72-9 indole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 123191-00-4 1-(triisopropylsilyl)-1H-indole 
• 1484-27-1 3-bromoindole 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 942070-45-3 tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate 
• 476004-82-7 3?(4,4,5,5?tetramethyl?1,3,2?dioxaborolan?2?yl)?1?(triisopropylsilyl)?1H?indole 

Downstream Products

• 56366-31-5 3-(2-nitrophenyl)-1H-indole 
• 937366-57-9 3-(2,5-dichloropyrimidine-4-yl)-1H-indole 

Relevant articles and documents

Ni-Catalyzed Traceless, Directed C3-Selective C-H Borylation of Indoles

A highly efficient and general protocol for traceless, directed C3-selective C-H borylation of indoles with [Ni(IMes)2] as the catalyst is reported. Activation and borylation of N-H bonds by [Ni(IMes)2] is essential to install a Bpin moiety at the N-position as a traceless directing group, which enables the C3-selective borylation of C-H bonds. The N-Bpin group which is formed is easily converted in situ back to an N-H group by the oxidative addition product of [Ni(IMes)2] and in situ-generated HBpin. The catalytic reactions are operationally simple, allowing borylation of a variety of substituted indoles with B2pin2 in excellent yields and with high selectivity. The C-H borylation can be followed by Suzuki-Miyaura cross-coupling of the C-borylated indoles in an overall two-step, one-pot process providing an efficient method for synthesizing C3-functionalized heteroarenes.

CONDENSED CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

A condensed cyclic compound and an organic light-emitting device including the same, the condensed cyclic compound being represented by the following Formula 1:

Boc groups as protectors and directors for ir-catalyzed C-H borylation of heterocycles

(Chemical Equation Presented) Ir-catalyzed C-H borylation is found to be compatible with Boc protecting groups. Thus, pyrroles, indoles, and azaindoles can be selectively functionalized at C-H positions β to N. The Boc group can be removed on thermolysis