4-CYANO-7-AZAINDOLE

White solid

Step 1: lH-pyrrolo [2, 3-6] pyridine-4-carbonitrile (21)To degassed N, N-dimethylacetamide (200 mL), compound 12 (30.0 g, 196.7 mmol), zinc cyanide (23.1 g, 196.7 mmol), zinc powder (1.28 g, 19.67 mmol), tris(dibenzylideneaceton)- dipalladium (3.6 g, 3.93 mmol) and diphenylphosphinoferrocene (4.36 g, 7.86 mmol) were added and the mixture was heated at 120 °C for 18 h. After cooling to room temperature, reaction mixture was poured on crushed ice (1.5 kg) and resulting solid was filtered. Solid was taken in ethyl acetate (2 x 1500 mL) and stirred for 0.5 h and filtered. Filtrate was concentrated, residue was crystallized from ethyl acetate and filtered to afford 1H- pyrrolo[2, 3-.pound.] pyridine-4-carbonitrile 22.0 g (78percent). 1HNMR (400MHZ, DMSO-dA suspension of 4-chloro-7-azaindole (Int-6, 18.2 g, 119 mmol) in dimethylacetamide (100 mL) was degassed and then filling with nitrogen. To this suspension was added zinc powder (720 mg, 11 mmol), diphenylphosphinoferrocene (2.1 g, 3.8 mmol), zinc cyanide (8.2 g, 69.8 mmol), and tris(dibenzylideneacetone) dipalladium (1.74 g, 1.9 mmol) at room temperature. The mixture was heated at 120 [001218] (i) Production of lH-pyrrolo[2, 3-b]pyridine-4-carbonitrile[001219] A mixture of 4-chloro-lH-pyrrolo[2, 3-b]pyridine (3.1 g, 20 mmol), zinc cyanide (1.4 g, 12 mmol), zinc (130 mg, 2.0 mmol), tris(dibenzylideneacetone)dipalladium(0) (370 mg, 0.40 mmol), 1, 1'- bis(diphenylphosphino)ferrocene (440 mg, 0.80 mmol) and N, N-dimethylacetamide (20 mL) was stirred at 120Part 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 (74percent) 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).

Molecular Weight:143.15
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:143.048347172
Monoisotopic Mass:143.048347172
Topological Polar Surface Area:52.5
Heavy Atom Count:11
Complexity:193
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes