Products Categories
CAS No.: | 937366-54-6 |
---|---|
Name: | PINACOL ESTER INDOLE-5-BORONIC ACID |
Article Data: | 6 |
Molecular Structure: | |
Formula: | C14H18BNO2 |
Molecular Weight: | 243.113 |
Synonyms: | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole; |
Density: | 1.11 |
Boiling Point: | 396.0±15.0 °C(Predicted) |
PSA: | 34.25000 |
LogP: | 2.46710 |
indole
bis(pinacol)diborane
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
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
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
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
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
Conditions | Yield |
---|---|
at 180℃; for 0.75h; | 64% |
indole
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
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
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride |
1-(triisopropylsilyl)-1H-indole
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
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
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
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 |
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
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
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
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 |
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
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. |