ChemicalBook CAS DataBase List [3,3'-Bipyridin]-5-ylboronic acid

[3,3'-Bipyridin]-5-ylboronic acid synthesis

3synthesis methods

Product Name:[3,3'-Bipyridin]-5-ylboronic acid
CAS Number:1034541-67-7
Molecular formula:C10H9BN2O2
Molecular Weight:200

5419-55-6
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15862-22-3 Synthesis

15862-22-3
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1034541-67-7
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Yield:1034541-67-7 37%

Reaction Conditions:

Stage #1: Triisopropyl borate;5-bromo-3,3'-bipyridinewith n-butyllithium in tetrahydrofuran;hexanes;toluene at -40 - -20; for 0.5 h;
Stage #2: with hydrogenchloride;water in tetrahydrofuran;hexanes;toluene at -20 - 20;
Stage #3: with sodium hydroxide;water in tetrahydrofuran;hexanes;toluene; pH=7.6;

Steps:

2

Compound 20 - A three-necked round-bottomed flask equipped with a thermometer was charged with compound 19 (1.2 g, 5.1 mmol), toluene (8 mL), THF (3 mL), and trisopropylborate (1.4 mL, 6.0 mmol). After cooling to - 40 ⁰C (dry ice/acetone), ?-butyllithium (1.6 M in hexanes, 3.75 mL) was slowly added over the course of 30 min. The reaction was then allowed to warm to - 20 ⁰C, and HCl (2M, 5 mL) was added. When the reaction reached room temperature, the aqueous layer was removed and adjusted to pH 7.6 with NaOH (3M, 2 mL), saturated with NaCl, and extracted with THF (3 x 6 mL). The THF layers were combined, dried with MgSO₄, evaporated to an oil, diluted with CH₃CN (40 mL), and heated at 70 ⁰C for 30 min. The solution was let crystallize at 4 ⁰C for 72 h. The yellow solid was filtered, washed with ice-cold CH₃CN, and air-dried (0.38 g, 37%). ¹H NMR (CD₃OD, 500 MHz) δ 7.61 (dd, J = 7.7, 4.9 Hz₅ IH), 8.21 (dt, J = 8.0, 1.9 Hz, IH), 8.60 (s, IH), 8.65 (dd, J= 4.9, 1.4 Hz, IH), 8.72 (s, IH), 8.89 (d, J= 2.2 Hz, IH), 8.91 (d, J= 1.9 Hz, IH).

References:

WO2008/137604,2008,A1 Location in patent:Page/Page column 4; 31-32; 40

1692-25-7
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1034541-67-7
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References

625-92-3 Synthesis

625-92-3
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1034541-67-7
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References