Alternatived Products of [ 942070-06-6 ]
Product Details of [ 942070-06-6 ]
CAS No. : | 942070-06-6 |
MDL No. : | MFCD08063135 |
Formula : |
C10H14BBrO2S
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | XOLVNUOSAPZSLF-UHFFFAOYSA-N |
M.W : |
289.00
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Pubchem ID : | 53398058 |
Synonyms : |
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Safety of [ 942070-06-6 ]
Application In Synthesis of [ 942070-06-6 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Downstream synthetic route of [ 942070-06-6 ]
- 1
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[ 872-31-1 ]
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[ 25015-63-8 ]
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[ 942070-06-6 ]
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[ 1040281-99-9 ]
Yield | Reaction Conditions | Operation in experiment |
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With 4,4'-di(tert-butyl)-2,2'-dipyridyl In hexane at 20℃; for 1h; Title compound not separated from byproducts.; |
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- 2
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[ 942070-06-6 ]
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6-(3-bromo-2-chlorophenyl)-2-methoxynicotinaldehyde
[ No CAS ]
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6-(3-(4-bromothiophen-2-yl)-2-chlorophenyl)-2-methoxynicotinaldehyde
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
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With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 85℃; Inert atmosphere; |
597
A 40 mL reaction vial, fitted with a stir bar, was charged with 2-(4-bromothiophen-2-yl)-4,4,5,5- tetramethyl- 1,3 ,2-dioxaborolane (0.150 g), 6-(3 -bromo-2-chlorophenyl)-2-methoxynicotinaldehyde (0.203 g), Pd(dppf) (0.0 18 g) and potassium carbonate (0.143 g). DriSolv 1,4-Dioxane (5 mL) and distilled water (0.5 mL) were then added by syringe, and the mixture de-gassed by bubbling argon for 5 mm while mixing. The reaction vial was then sealed with a septum cap and the reaction heated to 85 °C using a heating block, the reaction was monitored by LC/MS. Upon complete consumption of starting material, saturated NaC1 in water was added and the reaction mixture was extracted three times with ethylacetate. The organic layers were collected, volatiles removed and cmde mixture purified by silica gel column chromatography. LCMS mlz 410.00 M+1. |
- 3
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[ 942070-06-6 ]
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[ 1066-54-2 ]
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trimethyl((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl)ethynyl)silane
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
24% |
With piperidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; |
E Preparation E: trimethyl((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-3-yl)ethynyl)silane
A mixture of 4-bromothiophene-2-boronic acid pinacol ester (0.500 9; 1.57 mmol), trimethylsilylacetylene (0.333 mL; 2.36 mmol), piperidine (0.466 mL; 4.72 mmol), Cul (0.0299 g, 0.157 mmol) and Pd(PPhs), (0.09 g, 0.078 mmol) in THF (7.9 mL) was stirred overnight at rt. The mixture was diluted in EA (50 mL) and filtered through a short pad of silica gel. The filtrate was concentrated in vacuo and the evaporation residue was purified by CC (Hept-EA gradient) to afford the title compound (0.114 g, 24% yield) as an orange brownoil. 1H NMR (DMSO-d) 8: 8.17 (d, J = 1.1Hz, 1H); 7.48 (d, J = 1.1Hz, 1H); 1.28 (s, 12H); 0.21 (s, 9H). |
- 4
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[ 872-31-1 ]
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[ 73183-34-3 ]
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[ 942070-06-6 ]
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[ 1040281-99-9 ]
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C16H25B2BrO4S
[ No CAS ]
Yield | Reaction Conditions | Operation in experiment |
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Stage #1: bis(pinacol)diborane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran Inert atmosphere; Glovebox;
Stage #2: 3-Bromothiophene In tetrahydrofuran at 65℃; for 24h; Sealed tube; Inert atmosphere; regioselective reaction; |
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Reference:
[1]Hartwig, John F.; Karmel, Caleb; Kharitonova, Elena V.; Rubel, Camille Z.
[Angewandte Chemie - International Edition, 2020, vol. 59, # 15, p. 6074 - 6081][Angew. Chem., 2020, vol. 132, p. 6130 - 6137,8]
- 5
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[ 872-31-1 ]
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[ 73183-34-3 ]
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[ 942070-06-6 ]
Yield | Reaction Conditions | Operation in experiment |
95% |
Stage #1: bis(pinacol)diborane With 5-methyl-2-(thiophen-3-yl)pyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer In tetrahydrofuran at 20℃; for 0.0333333h; Inert atmosphere; Glovebox;
Stage #2: 3-Bromothiophene In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction; |
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