II.Br[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.Br[C:43]1[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=1>CN(C=O)C.[Zn].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]>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:43]2[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=2)=[CH:6][CH:7]=1
Zinc (0.976 g, 14.9 mmol) and iodine (0.025 g, 0.100 mmol) were added to a flame-dried flask (25 mL) and heated with a heat gun under vacuum for 10 min. The flask was cooled to 0° C. and DMF (5 mL) was added. 1-(Bromomethyl)-4-methoxybenzene (1.43 mL, 9.95 mmol) was added as a solution in DMF (5 mL) and the mixture was stirred for 20 min at 0° C., then RT for 20 min. S-Phos (0.490 g, 1.19 mmol), Pd2 dba3 (0.273 g, 0.299 mmol), and 3-bromopyridine (0.976 mL, 9.95 mmol) were added and the mixture was heated 60° C. for 1 h. The mixture was cooled to RT, filtered through celite, concentrated in vacuo, and purified by column chromatography to give 3-(4-methoxybenzyl)pyridine as a light-yellow oil. MS (ESI) m/z: Calculated: 199.1; Observed: 200.3 (M++1).
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