4-{6-Chloroimidazo[1,2-b]pyridazin-3-yl}benzonitrile synthesis

4synthesis methods

Product Name:4-{6-Chloroimidazo[1,2-b]pyridazin-3-yl}benzonitrile
CAS Number:1082604-63-4
Molecular formula:C13H7ClN4
Molecular Weight:254.67

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126747-14-6 Synthesis

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4-{6-Chloroimidazo[1,2-b]pyridazin-3-yl}benzonitrile

1082604-63-4
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Yield:1082604-63-4 98%

Reaction Conditions:

with tetrakis(triphenylphosphine) palladium⁽⁰⁾;sodium carbonate in water;N,N-dimethyl-formamide at 90; for 18 h;Inert atmosphere;

Steps:

1

Step 1 : To a solution of 6-chloro-3-iodoimidazo[l,2-b]pyridazine (1.00 g, 3.58 mmol) in a mixture of DMF (20 mL) and water (1 mL) under inert atmosphere, were added Na₂C0₃ (759 mg, 7.16 mmol), 4-cyanophenylboronic acid (885 mg, 5.37 mmol) and Pd(PPh₃)₄ (414 mg, 0.358 mmol). The resulting mixture was stirred at 90 °C for 18 h and quenched with ice water. The precipitate was isolated by filtration and dried in vacuo to afford 4-(6- chloroimidazo[l,2-6]pyridazin-3-yl)benzonitrile (897 mg, 98%) as a yellow solid. 1H NMR ^{FontWeight="Bold" FontSize="10"}--^·.·^· (400 MHz, CDC1₃) δ 8.24-8.21 (m, 2H), 8.18 (s, 1H), 8.02 (d, J= 9.4 Hz, 1H), 7.81-7.79 (m, 2H), 7.45 (d, J = 9.4 Hz, lH); MS (ESI) m/z 255 [C₁₃H₇C1N₄ + H]⁺.