6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline synthesis
- Product Name:6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline
- CAS Number:1167418-13-4
- Molecular formula:C14H17BN2O2
- Molecular Weight:256.11
50998-17-9
73183-34-3
1167418-13-4
To a solution of 6-bromoquinoxaline (418 mg, 2.00 mmol, 1.00 eq.) in dioxane (10 mL) at 23 °C was sequentially added PdCl2(dppf)-CH2Cl2 (163 mg, 0.200 mmol, 0.100 eq.), bis(pinacolide)diboron (610 mg, 2.40 mmol, 1.20 eq.) and KOAc (392 mg, 4.00 mmol, 2.00 equiv). The reaction mixture was stirred at 90 °C for 1.5 h, subsequently cooled to 23 °C and concentrated in vacuum. The residue was dissolved with CH2Cl2 and filtered through a diatomaceous earth plug. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography with hexane/EtOAc (4:1, v/v) as eluent to give 500 mg of quinoxaline-6-boronic acid pinacol ester as a colorless solid (98% yield). Thin layer chromatography Rf = 0.45 (unfolding agent: hexane/EtOAc, 1:1, v/v). Nuclear magnetic resonance hydrogen spectrum (1H NMR, 500 MHz, CDCl3, 23°C) δ: 8.86-8.82 (m, 2H), 8.59 (s, 1H), 8.12 (dd, J = 8.0 Hz, 2.0 Hz, 1H), 8.06 (d, J = 8.0 Hz, 1H), 1.37 (s, 12H). Nuclear magnetic resonance carbon spectrum (13C NMR, 125 MHz, CDCl3, 23°C) δ: 145.53, 145.03, 144.37, 142.41, 137.31, 134.75, 131.90 (br), 128.44, 84.36, 24.86. high-resolution mass spectra (HRMS-FIA) m/z: [M + H]+ Calculated value 257.14558, measured value 257.14440.
50998-17-9
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73183-34-3
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$6.00/5g
1167418-13-4
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$42.00/100mg
Yield:1167418-13-4 98%
Reaction Conditions:
with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;potassium acetate in 1,4-dioxane at 90; for 1.5 h;Inert atmosphere;
References:
Furuya, Takeru;Ritter, Toblas [Organic Letters,2009,vol. 11,# 13,p. 2860 - 2863] Location in patent:supporting information; experimental part
5448-43-1
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73183-34-3
585 suppliers
$6.00/5g
1167418-13-4
88 suppliers
$42.00/100mg