[Cl:1][C:2]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Br[C:20]1[CH:27]=[N:26][CH:25]=[C:24]([F:28])[C:21]=1[CH:22]=[O:23].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[C:8]([C:20]2[CH:27]=[N:26][CH:25]=[C:24]([F:28])[C:21]=2[CH:22]=[O:23])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]
To the solution of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (264 mg, 1.00 mmol), 3-bromo-5-fluoroisonicotinaldehyde (204 mg, 1.00 mmol) and PdCl2(PPh3)2 (56 mg, 0.08 mmol) in DMF (3 mL) was added 2M Na2CO3 solution (1.50 ml, 3.00 mmol) under nitrogen atmosphere. The mixture was stirred and heated at 100° C. for 4 hrs. After letting cool to room temperature, solvent was removed in vacuo. The resulting residue was dissolved in DCM and saturated NH4Cl solution. After extraction and separation, the combined extracts were concentrated and purified by SNAP10 g (10% MeOH/DCM 0-15% gradient) to give 2-chloro-4-(5-fluoro-4-formylpyridin-3-yl)benzonitrile (47 mg, 18%) as a white solid; ESI-MS m/z: 293 [M+MeOH+1]+, Retention time 1.15 min. 1H-NMR (CDCl3, 400 MHz) δ 7.33 (dd, J=8.0, 1.6 Hz, 1H), 7.50 (d, J=1.6 Hz, 1H), 7.78 (d, J=8.0 Hz, 1H), 8.49 (s, 1H), 8.78 (d, J=1.2 Hz, 1H), 10.27 (s, 1H).
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