4-CYANO-7-AZAINDOLE synthesis
- Product Name:4-CYANO-7-AZAINDOLE
- CAS Number:344327-11-3
- Molecular formula:C8H5N3
- Molecular Weight:143.15
557-21-1
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344327-11-3
Step 1: To degassed N,N-dimethylacetamide (200 mL), 4-chloro-7-azaindole (30.0 g, 196.7 mmol), zinc cyanide (23.1 g, 196.7 mmol), zinc powder (1.28 g, 19.67 mmol), tris(dibenzylideneacetone)dipalladium (3.6 g, 3.93 mmol) and diphenylphosphino ferrocene (4.36 g, 7.86 mmol). The reaction mixture was heated at 120 °C for 18 hours. After completion of the reaction, it was cooled to room temperature and the mixture was poured into crushed ice (1.5 kg) and the solid product was collected by filtration. The solid product was washed with ethyl acetate (2 x 1500 mL) and filtered after stirring for 0.5 h at a time. The filtrates were combined, concentrated and crystallized from ethyl acetate to give 1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (22.0 g, 78% yield).1H NMR (400 MHz, DMSO-d6): δ 12.20 (br s, 1H), 8.41 (d, J = 4.8 Hz, 1H), 7.84 (s, 1H), 7.56 (d, J = 4.8 Hz, 1H), 6.65 (d, J = 1.6 Hz, 1H).
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Yield: 74%
Reaction Conditions:
tris-(dibenzylideneacetone)dipalladium(0);1,1'-bis(diphenylphosphino)ferrocene in water;N,N-dimethyl-formamide at 90; for 20 h;
Steps:
13.3
Part 3: [0197] 1H-Pyrrolo[2,3-b]pyridine-4-carbonitrile: To a solution of (4.7 g, 19.3 mmol) of 4-Iodo-1H-pyrrolo[2,3-b]pyridine in degassed DMF (25 mL) was added Pd2(dba)3 (10 mg), dppf (15 mg), degassed H2O (2 mL) and Zn(CN)2 (1.4 g, 11.6 mmol). The mixture was stirred at 90 C. under nitrogen for 20 hr, then cooled to 70 C. and 75 mL of a 4:1:4 mixture of saturated NH4Cl:NH4OH:H2O was added. The mixture was stirred at 5 C. for 20 min. and the resulting precipitate filtered off, washed with 75 mL 4:1:5 mixture of saturated NH4Cl:NH4OH:H2O, 500 mL H2O and 100 mL toluene, then dried in vacuo to give 2.06 g (74%) 1H-Pyrrolo[2,3-b]pyridine-4-carbonitrile. MS (ES+): 143 [MH+]. 1H NMR (DMSO-d6, 400 MHz): δ 6.65 (d, 1H, J=3.2), 7.56 (d, 1H, J=4.8 Hz), 7.84 (d, 1H, J=4.0 Hz), 8.40 (d, 1H, J=4.8 Hz).
References:
Wynne, Graham Michael;Doyle, Kevin;Ahmed, Saleh;Li, An-Hu;Keily, John Fraser;Rasamison, Chrystelle Marie;Pegg, Neil Anthony;Saba, Imaad;Thomas, Claire;Smyth, Don;Sadiq, Shazia;Newton, Gary;Dawson, Graham;Crew, Andrew Phillip;Castelhano, Arlindo Lucas US2004/186124, 2004, A1 Location in patent:Page/Page column 14
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344327-11-3
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