Cl[C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[C:9]#[N:10])[NH2:5].[F-].[Cs+].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN1C(=O)CCC1.CCOC(C)=O.Cl[Pd](Cl)(P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)P(C1CCCCC1)(C1CCCCC1)C1CCCCC1>[C:9]([C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[CH:3][C:2]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)#[N:10]Commercially available 3-chloro-4-cyanoaniline (305 mg, 2.0 mmol) was dissolved in NMP (8 mL), and CsF (608 mg, 4.0 mmol), phenyl boronic acid (268 mg, 2.2 mmol) and dichlorobis(tricyclohexylphosphino)palladium (73 mg, 0.1 mmol) were added. The reaction was then heated to 100° C. for 16 h. After cooling to rt, the reaction mixture was taken up in EtOAc, washed with water (2×), dried (Na2SO4), concentrated under reduced pressure, and purified by silica gel flash chromatography eluting with EtOAc/hexanes (1:1) to give compound 47A (371 mg, 96%) as a yellow solid. LC/MS m/z 195 [M+H]+.
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