Preparation method of 6-cyano-7-azaindole and derivative thereof
A technology for azaindole and its derivatives, which is applied in the field of preparation of 6-cyano-7-azaindole and its derivatives, can solve the problems of unsuitable large-scale preparation and dangerous reagents, and achieve low environmental impact, High yield and easy reaction operation
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Embodiment 1
[0042] Synthesis of compound I:
[0043]
[0044] Disperse 6-bromo-7-azaindole (V, 10.00 g, 0.051 mol, 1.0 equiv.) in 100 mL N,N-dimethylacetamide, add potassium ferrocyanide (9.35 g, 0.025 mol, 0.5 equiv.), palladium acetate (0.57 g, 2.54 mmol, 5 mol%), triethylenediamine (DABCO, 0.85 g, 7.62 mmol, 15 mol%). After the addition, the temperature was raised to 120° C. for 16 hours, and TLC detected that the reaction was complete. After cooling down to room temperature, the reaction solution was poured into 400 mL of ice water, filtered, extracted twice with ethyl acetate (100 mL*2), and the organic phases were combined. The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain 5.92 g of a yellow solid, yield: 81.6%.
[0045] 1 H NMR (400MHz, CDCl 3 ) δ (ppm): 12.27 (s, 1 H), 8.19 (d, J = 7.96 Hz, 1 H), 7.85 (dd, J = 3.40, 2.36 Hz, 1 H), 7.63 (d, J = 8.04 Hz, 1 H), 6.65 (dd, J = 3.44, 1.44 H...
Embodiment 2
[0048] Synthesis of compound I:
[0049]
[0050] 6-Bromo-7-azaindole (V, 10.00 g, 0.051 mol, 1.0 equiv.) was dispersed in 100 mL N,N-dimethylformamide, and potassium ferrocyanide trihydrate (6.46 g , 0.015 mol, 0.3 equiv.), palladium acetate (0.23 g, 1.02 mmol, 2 mol%), triethylenediamine (DABCO, 0.46 g, 4.08 mmol, 8 mol%). After the addition, the temperature was raised to 100°C for 24 hours of reaction. After the reaction was complete by TLC, it was lowered to room temperature, and the reaction solution was poured into 400 mL of ice water, filtered, extracted twice with ethyl acetate (100 mL *2), and the organic phases were combined. The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain 4.98 g of a light yellow solid, yield: 68.2%.
[0051] 1 H NMR (400MHz, CDCl 3 ) δ (ppm): 12.27 (s, 1 H), 8.19 (d, J = 7.96 Hz, 1 H), 7.85 (dd, J = 3.40, 2.36 Hz, 1 H), 7.63 (d, J = 8.04 Hz, 1 H), 6.65...
Embodiment 3
[0053] Synthesis of compound II:
[0054]
[0055] 1-Benzoyl-6-bromo-7-azaindole (VII, 14.20 g, 0.047 mol, 1.0 equiv.) was dispersed in 100 mL N,N-dimethylacetamide, and potassium ferrocyanide ( 8.68 g, 0.024 mol, 0.5 equiv.), palladium acetate (0.53g, 2.35 mmol, 5 mol%), triethylenediamine (DABCO, 0.79 g, 7.05 mmol, 15 mol%). After the addition, the temperature was raised to 100° C. for 24 hours, and TLC detected that the reaction was complete. After cooling down to room temperature, the reaction solution was poured into 400 mL of ice water, filtered, extracted twice with ethyl acetate (100 mL *2), and the organic phases were combined. The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain 10.32 g of a yellow solid, yield: 88.4%.
[0056] 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 8.04-8.02 (m, 2H), 7.80-7.78 (m, 2H), 7.70-7.66 (m, 1H), 7.60-7.51 (m, 3H), 6.77 (d, J = 3.96 Hz, 1H).
[0057] LC...
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