[C:1]([C:4]1[C:5](Br)=[N:6][CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)#[CH:12].C(N(CC)CC)C.[Cl-]>CN(C=O)C.C(Cl)Cl>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]#[C:12][C:5]1[C:4]([C:1](=[O:3])[CH3:2])=[CH:9][CH:8]=[CH:7][N:6]=1
Step 1 (=Reaction 1): 750 mg 3-Acetyl-2-bromopyridin, 550 μL 2-ethynyl-pyridine, 765 μL triethylamin, 255 mg triphenylphosphinpalladium(II) chlorid, 17 mg Cu(I)I were suspended in 10 mL DMF under argon atmosphere and stirred for 2 h at 25° C. The mixture was diluted with DCM and extracted with diluted aq. NH3 and saturated NH4Cl solution. The organic phase was concentrated and the mixture separated via FCC (100 g SiO2, cyclohexane cyclohexane/ethylacetate 35:65) to yield 455 mg 1-(2-(pyridin-2-ylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS: Rt=0.88 min (methode E) M+H=223.
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