[C:1]([C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([O:9][CH3:10])=[N:7][CH:8]=1)#[CH:2].ClCCl.I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23]>C(N(CC)CC)C.C(OCC)(=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.[Cu]I>[CH3:10][O:9][C:6]1[C:5]([O:11][CH3:12])=[CH:4][C:3]([C:1]#[C:2][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])=[CH:8][N:7]=1
Bis(triphenylphosphine)palladium(II) dichloride (50 mg, 0.07 mmol), copper (I) iodide (25 mg, 0.13 mmol) and 5-ethynyl-2,3-dimethoxypyridine (Intermediate 32) (500 mg, 3.1 mmol) were suspended in degassed triethylamine (5 ml) and dichloromethane (5 ml) to give a brown suspension. To this was added 1-iodo-2-methylbenzene (670 mg, 3.1 mmol) by syringe and the reaction was allowed to stir for 16 hours before being diluted with ethyl acetate and washed with brine. The crude material was purified by column chromatography (SiO2; 0-10% ethyl acetate in petrol) to afford 2,3-dimethoxy-5-[(2-methylphenyl)ethynyl]pyridine (437 mg, 56% yield).
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