365564-11-0

Basic information

• Product Name: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole
• Synonyms: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole;1-(Triisopropylsilyl)-1H-...;1-(Triisopropylsilyl)-1H-pyrrole-3-boronic acid pinacol ester;1H-Pyrrole, 3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-Methylethyl)silyl]-;3-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-Methylethyl)silyl]-1H-pyrrole;N-TIPS pyrrole-3-boronic acid pinacol ester;1-(triisopropylsilyl)-1H-pyrrol-3-ylboronic acid pinacol ester;3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(propan-2-yl)silyl]-1H-pyrrole
• CAS NO: 365564-11-0
• Molecular Formula: C₁₉H₃₆BNO₂Si
• Molecular Weight: 349
• Mol File: 365564-11-0.mol
• Article Data: 26

Chemical Properties

• Melting Point: 59 °C
• Boiling Point: 383.588°C at 760 mmHg
• Flash Point: 185.788°C
• Appearance: White to yellow/Powder or Solid
• Density: 0.941g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.477
• PKA: -2.53±0.70(Predicted)
• CAS DataBase Reference: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole(365564-11-0)
• EPA Substance Registry System: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole(365564-11-0)

Safety Data

• Hazardous Substances Data: 365564-11-0(Hazardous Substances Data)

Usage

General Description

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole is a chemical compound that is commonly used in the field of organic chemistry. It is a boronate ester derivative of 1-(triisopropylsilyl)-1H-pyrrole, which is a versatile building block for the synthesis of various organic compounds. The presence of both boron and silicon in the molecule makes it a useful reagent for cross-coupling reactions, as well as for the formation of complex organic structures. 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole is often used as a reagent in the synthesis of pharmaceuticals, agrochemicals, and other biologically active molecules. Its unique structure and reactivity make it a valuable tool in the field of chemical synthesis.

InChI:InChI=1/C19H36BNO2Si/c1-14(2)24(15(3)4,16(5)6)21-12-11-17(13-21)20-22-18(7,8)19(9,10)23-20/h11-16H,1-10H3

Synthetic route

N-triisopropylsilylpyrrole (87630-35-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
With 1-(2-borylphenyl)-2,2,6,6-tetramethylpiperidine dimer In chloroform at 80℃; for 16h;	98%
With Cp*Rh(η4-C6Me6) In cyclohexane at 150℃; for 41h;	81%
Stage #1: N-triisopropylsilylpyrrole With 2,6-dimethylpyridine; aluminum (III) chloride; boron trichloride In n-heptane; dichloromethane at 20℃; for 16h; Inert atmosphere; Stage #2: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With triethylamine In n-heptane; dichloromethane for 0.25h; Inert atmosphere;	52%
With poly((2-(piperidin-1-ium-1-yl)-5-vinylphenyl)trifluoroborate) In chloroform-d1 at 90℃; for 16h; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube;

2,3-dimethyl-2,3-butane diol (76-09-5) + C6Cl4O2BN(C2H5)3(1+)*AlCl4(1-)=C6Cl4O2BN(C2H5)3[AlCl4] + N-triisopropylsilylpyrrole (87630-35-1) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
With Et3N In dichloromethane byproducts: Et3NH-AlCl4; to borenium cation made in situ (in Schlenk, to soln. Et2N (CH2Cl2) added Cl4CatBCl, AlCl3; stirred) at 20°C arene added (CH2Cl2); excessEt3N added; pinacol added; stirred for 32 h;; (11)B (1H) NMR; volatiless remowed under vac; extracted (hexane); filtered through silica; removal of solvent;;	95%

2,3-dimethyl-2,3-butane diol (76-09-5) + 3-(1,3,2-benzodioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
With triethylamine In dichloromethane for 3h;	90%
With triethylamine In toluene at 20℃; for 1h; Schlenk technique;	45%
With triethylamine In dichloromethane for 1h; Inert atmosphere;	101 mg
With triethylamine at 0 - 20℃; for 1h; Inert atmosphere;
With triethylamine In 1,2-dichloro-ethane at 20℃; Schlenk technique; Inert atmosphere;

2,3-dimethyl-2,3-butane diol (76-09-5) + C13H24BCl2NSi (1416243-53-2) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
With triethylamine at 20℃; for 0.5h;	90%

2,3-dimethyl-2,3-butane diol (76-09-5) + N-triisopropylsilylpyrrole (87630-35-1) + boron trichloride (10294-34-5) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
With AlCl3; 2,6-lutidine In dichloromethane 1:1 mixt. of BCl3 and AlCl, pinacol (2.3-3.0 equiv.) and lutidine (15 equiv.) for 14 h;	90%

2,3-dimethyl-2,3-butane diol (76-09-5) + N-triisopropylsilylpyrrole (87630-35-1) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
Stage #1: N-triisopropylsilylpyrrole With 2,6-dimethylpyridine; aluminum (III) chloride; boron trichloride In n-heptane; dichloromethane at 20℃; for 14h; Inert atmosphere; Stage #2: 2,3-dimethyl-2,3-butane diol With triethylamine In n-heptane; dichloromethane at 20℃; for 0.5h; Inert atmosphere;	90%

2,3-dimethyl-2,3-butane diol (76-09-5) + C6H4O2BN(C2H5)3(1+)*AlCl4(1-)=C6H4O2BN(C2H5)3[AlCl4] + N-triisopropylsilylpyrrole (87630-35-1) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
With Et3N In dichloromethane byproducts: Et3NH-AlCl4; to borenium cation made in situ (in Schlenk, to soln. Et2N (CH2Cl2) added CatBCl, AlCl3; stirred) at 20°C arene added (CH2Cl2); excess Et3N added; pinacol added; stirred for 32 h;; (11)B (1H) NMR; volatiless remowed under vac; extracted (hexane); filtered through silica; removal of solvent;;	89%

3-bromo-1-triisopropylsilanyl-1H-pyrrole (87630-36-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; triethylamine; dichloro bis(acetonitrile) palladium(II) In toluene at 90℃; for 18h;	85%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; triethylamine; dichloro bis(acetonitrile) palladium(II) In toluene at 90℃; for 18h;	85%
With dichloro bis(acetonitrile) palladium(II); triethylamine In toluene 1.2 equiv. pinacol borane react. catalyzed by 3% (PdCl2(CH3CN)2), 9% dialkylmonophosphino biaryl (toluene) at 90°C;	79%

3-iodo-1-(triisopropylsilyl)-1H-pyrrole (117270-91-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); triethylamine In toluene at 20 - 90℃; Inert atmosphere;	80%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); triethylamine In toluene

N-triisopropylsilylpyrrole (87630-35-1) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
bis(1,5-cyclooctadiene)diiridium(I) dichloride; 4,4'-di-tert-butyl-2,2'-bipyridine In octane at 80℃; for 16h;	79%
With [IrCl(COD)]2 In octane at 80℃; for 48h; Inert atmosphere;	77%
With 4,4'-di-tert-butyl-2,2'-bipyridine; bis(1,5-cyclooctadiene)diiridium(I) dichloride In hexane at 100℃; for 0.833333h; microwave irradiation;
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4′-di-(tert-butyl)-2,2′-bipyridyl In tetrahydrofuran at 80℃; for 24h; High pressure; Inert atmosphere; regioselective reaction;

N-triisopropylsilylpyrrole (87630-35-1) + bis(pinacol)diborane (73183-34-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In tetrahydrofuran at 15 - 70℃; for 16.5h; Inert atmosphere;	71%

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1195-66-0) + 3-bromo-1-triisopropylsilanyl-1H-pyrrole (87630-36-2) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
With CH3CH2CH2CH2Li In tetrahydrofuran treatment of pyrrole deriv. with butyllithium in THF at -78°C, addn. of borolane deriv.;	24%
With CH3CH2CH2CH2Li In tetrahydrofuran treatment of pyrrole deriv. with butyllithium in THF at -78°C, addn. of borolane deriv.; not isolated;
Stage #1: 3-bromo-1-triisopropylsilanyl-1H-pyrrole With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 20℃;

triisopropylsilyl chloride (13154-24-0) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran 2: N-bromosuccinimide / acetonitrile 3: 85 percent / Et3N; 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl / PdCl2(CH3CN)2 / toluene / 18 h / 90 °C View Scheme
Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran / -78 - 20 °C / Inert atmosphere 2: N-Bromosuccinimide / tetrahydrofuran / -78 - 20 °C / Inert atmosphere 3: bis(acetonitrile)palladium(II) chloride; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; triethylamine / toluene / 80 - 90 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C / Inert atmosphere 1.2: 1 h / 0 °C 2.1: N-Bromosuccinimide / tetrahydrofuran / 5 h / -70 °C / Inert atmosphere 2.2: 1 h / -70 - 20 °C / Inert atmosphere 3.1: dichloro bis(acetonitrile) palladium(II); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; triethylamine / toluene / 16 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -65 °C 1.2: 4 h / -65 °C 2.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 16.5 h / 15 - 70 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran 2: N-iodo-succinimide / acetone 3: triethylamine; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II) / toluene View Scheme

N-triisopropylsilylpyrrole (87630-35-1) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-bromosuccinimide / acetonitrile 2: 85 percent / Et3N; 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl / PdCl2(CH3CN)2 / toluene / 18 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride; triethylamine / dichloromethane / 20 °C / Inert atmosphere 1.2: 72 h / 20 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 1 h / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: triethylamine; aluminum (III) chloride / dichloromethane; water / Inert atmosphere 1.2: 72 h 2.1: triethylamine / dichloromethane / 3 h View Scheme

2,3-dimethyl-2,3-butane diol (76-09-5) + C19H24BCl4NO2Si → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
With triethylamine In dichloromethane for 1h; Inert atmosphere;

C14H26Si → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2,6-dimethylpyridine; aluminum (III) chloride; boron trichloride / n-heptane; dichloromethane / 14 h / 20 °C / Inert atmosphere 2: triethylamine / 0.5 h / 20 °C View Scheme

2,3-dimethyl-2,3-butane diol (76-09-5) + 2-chloro-1,3,2-benzodioxaborole (55718-76-8) + N-triisopropylsilylpyrrole (87630-35-1) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
Stage #1: 2-chloro-1,3,2-benzodioxaborole; N-triisopropylsilylpyrrole With aluminum (III) chloride; tricyclohexylphosphine In dichloromethane Inert atmosphere; Stage #2: 2,3-dimethyl-2,3-butane diol With triethylamine In dichloromethane Product distribution / selectivity; Irradiation;

3-bromo-1-triisopropylsilanyl-1H-pyrrole (87630-36-2) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); triethylamine In 1,4-dioxane for 10h; Inert atmosphere;	58 mg

C15H9ClFN5 + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → C28H33FN6Si

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 95℃; for 4h; Inert atmosphere;	100%

2-bromothiophene (1003-09-4) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 3-(thiophen-2-yl)-1-(triisopropyl-silanyl)-1H-pyrrole

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 100℃; for 2h; Suzuki-Miyaura cross-coupling;	99%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 100℃; for 2h; Suzuki-Miyaura reaction;	99%

5-bromo-1H-indole (10075-50-0) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 5-[1-(triisopropyl-silanyl)-1H-pyrrol-3-yl]-1H-indole

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 100℃; for 2h; Suzuki-Miyaura cross-coupling;	97%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 100℃; for 2h; Suzuki-Miyaura reaction;	97%

4-bromoisoquinoline (1532-97-4) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 4-[1-(triisopropylsilanyl)-1H-pyrrol-3-yl]isoquinoline

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 100℃; for 2h; Suzuki-Miyaura reaction;	93%

1-iodo-4-methoxy-2-nitrobenzene (58755-70-7) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 3-(4-methoxy-2-nitrophenyl)-1-(triisopropylsilyl)-1H-pyrrole

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 80℃; for 12h; Suzuki-Miyaura Coupling;	92%

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;	91%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 2.25h; Inert atmosphere;	70%
With tetrabutyl ammonium fluoride
With tetrabutyl ammonium fluoride In tetrahydrofuran

2-bromo-pyridine (109-04-6) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 2-[1-(triisopropyl-silanyl)-1H-pyrrol-3-yl]-pyridine (566931-86-0)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 100℃; for 2h; Suzuki-Miyaura cross-coupling;	91%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 100℃; for 2h; Suzuki-Miyaura reaction;	91%

2-iodophenylamine (615-43-0) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 2-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline (1126425-85-1)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 80℃; for 3h; Inert atmosphere;	91%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 35℃; for 12h; Suzuki-Miyaura coupling; Inert atmosphere;	85%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 80℃; for 2h; Suzuki-Miyaura Coupling; Inert atmosphere;	84%

1-bromo-3-chloro-2-nitrobenzene (59772-48-4) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 3-(3'-chloro-2'-nitrophenyl)-N-(TIPS)pyrrole (1126425-88-4)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 0℃; for 16h; Suzuki-Miyaura coupling; Inert atmosphere;	87%

2-bromoaniline (615-36-1) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 2-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline (1126425-85-1)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 100℃; for 16h; Suzuki-Miyaura coupling; Inert atmosphere;	85%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 80℃; for 12h; Suzuki-Miyaura Coupling;

4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (1251908-25-4) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 4-(1H-pyrrol-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 90℃; for 18h; Inert atmosphere;	84%

3-bromoquinoline (5332-24-1) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 3-[1-(triisopropylsilanyl)-1H-pyrrol-3-yl]quinoline

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 100℃; for 2h; Suzuki-Miyaura reaction;	83%

2-chloroquinoxaline (1448-87-9) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 2-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]quinoxaline

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 80℃; for 2h; Suzuki-Miyaura reaction;	83%

5-Chloro-2-thiophenecarboxaldehyde (7283-96-7) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 5-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]thiophene-2-carbaldehyde

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 80℃; for 2h; Suzuki-Miyaura reaction;	82%

N-(4-bromo-pyridin-3-yl)-2,2-dimethylpropanamide (239137-58-7) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → N-[4-(1H-pyrrol-3-yl)pyridin-3-yl]pivalamide (1095911-41-3)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate tribasic trihydrate In water; butan-1-ol at 100℃; Suzuki cross-coupling; Inert atmosphere;	82%

2-Chloro-6-bromoaniline (59772-49-5) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline (1126425-86-2)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 35℃; for 12h; Suzuki-Miyaura coupling; Inert atmosphere;	82%

2-nitrophenyl bromide (577-19-5) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 3-(2-nitrophenyl)-1-(triisopropylsilyl)-1H-pyrrole (1033282-26-6)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 35℃; for 12h; Suzuki-Miyaura coupling; Inert atmosphere;	81%

2-chloro-6-iodobenzoic acid (13420-63-8) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline (1126425-86-2) + C19H29ClN(15)NSi

Conditions

Yield

Stage #1: 2-chloro-6-iodobenzoic acid With sulfuric acid at 60℃; for 1h; Inert atmosphere; Stage #2: With [(15)N]sodium azide at 20℃; for 42h; Inert atmosphere; Stage #3: 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 20℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere;

A n/a B 81%

1,2-difluoro-4,5-dibromobenzene (64695-78-9) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 3,3'-(4,5-difluoro-1,2-phenylene)bis(1-(triisopropylsilyl)-1H-pyrrole)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; butan-1-ol at 80℃; for 7h; Suzuki-Miyaura Coupling; Inert atmosphere;	79%

1-(4-(6-((4-(6-bromoimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl)amino)pyridin-3-yl)piperazin-1-yl)ethan-1-one + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 1-(4-(6-((4-(6-(1H-pyrrol-3-yl)imidazo[1,2-a]pyridin-3-yl)pyrimidin-2-yl)amino)pyridin-3-yl)piperazin-1-yl)ethan-1-one

Conditions	Yield
With sodium carbonate In acetonitrile at 130 - 160℃; for 2h; Microwave irradiation;	79%

Upstream product

• 87630-35-1 N-triisopropylsilylpyrrole 
• 73183-34-3 bis(pinacol)diborane 
• 117270-91-4 3-iodo-1-(triisopropylsilyl)-1H-pyrrole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 55718-76-8 2-chloro-1,3,2-benzodioxaborole 
• 87630-36-2 3-bromo-1-triisopropylsilanyl-1H-pyrrole 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 13154-24-0 triisopropylsilyl chloride 
• 10294-34-5 boron trichloride 
• 1416243-53-2 C₁₃H₂₄BCl₂NSi 

Downstream Products

• 214360-77-7 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole 
• 1024028-95-2 1-[5-fluoro-3-(3-fluoro-benzyl)-7-(1-triisopropylsilanyl-1H-pyrrol-3-yl)-benzofuran-2-yl]-ethanone 
• 138900-57-9 3-phenyl-1-[tris(propan-2-yl)silyl]-1H-pyrrole 
• 1033282-26-6 3-(2-nitrophenyl)-1-(triisopropylsilyl)-1H-pyrrole 
• 1126425-85-1 2-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline 
• 1126425-86-2 2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline 
• 1126425-88-4 3-(3'-chloro-2'-nitrophenyl)-N-(TIPS)pyrrole 
• 138900-59-1 1-(triisopropylsilyl)-3-(4-methoxyphenyl)pyrrole 
• 953040-54-5 1-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole 

Relevant articles and documents

Preparation of novel pyridine-fused tris-heterocycles; pyrido[4,3-e]pyrrolo-/pyrido[4,3-e]furano[2,3-c]pyridazines and pyrido[3,4-b]pyrrolo[3,2-d]pyrrole

Three novel pyrido-fused tris-heterocycles have been prepared based on a Suzuki coupling and subsequent cyclisation approach. Pyrido[4,3-e]pyrrolo[2,3-c]pyridazine (3b, 77%) and pyrido[4,3-e]furano[2,3-c]pyridazine (5b, 76%) were obtained by intramolecular diazocoupling. Successful diazocoupling of furan (5b) is thus reported for the first time by NOBF4 generation of the diazonium intermediate. N-TIPS-pyrido[3,4-b]pyrrolo[3,2-d]pyrrole (TIPS-4b) was synthesised by thermal cyclisation of pyridyl nitrene in considerably higher yield (71%) than previously experienced from similar cyclisations, due to TIPS-activation.

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