Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]([C:20]3[C:24]4[CH:25]=[N:26][CH:27]=[CH:28][C:23]=4[N:22]([CH:29]([CH3:31])[CH3:30])[CH:21]=3)=[O:19])[CH:15]=[CH:14][N:13]=2)=[O:10])=[N:6][CH:7]=1.[CH3:32][N:33](C=O)C>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:32]([C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([C:18]([C:20]3[C:24]4[CH:25]=[N:26][CH:27]=[CH:28][C:23]=4[N:22]([CH:29]([CH3:31])[CH3:30])[CH:21]=3)=[O:19])[CH:15]=[CH:14][N:13]=2)=[O:10])=[N:6][CH:7]=1)#[N:33]A mixture of 2-(5-bromopyridin-2-yl)-N-(4-{[1-(propan-2-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl]carbonyl}pyridin-2-yl)acetamide (Example 237, 40 mg, 0.083 mmol), zinc cyanide (29 mg, 0.251 mmol), Pd2(dba)3 (3 mg, 0.003 mmol) and DPPF (7.5 mg, 0.013 mmol) in DMF (1 mL) was heated to 100° C. under microwave irradiation for 25 minutes. The reaction was cooled and diluted with ethyl acetate. The organic layer was collected, washed with water, brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified using preparative TLC eluting with 5% MeOH in DCM to afford the LCMS (5 minute run) Rt=2.78 minutes MS m/z 425 [M+H]+
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