[Br:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(Cl)Cl.CO.[BH4-].[Na+]>C1(C)C=CC=CC=1.CO>[CH2:17]([N:14]1[CH2:15][CH:16]=[C:11]([C:4]2[C:5]3[O:9][CH2:8][CH2:7][C:6]=3[CH:10]=[C:2]([Br:1])[CH:3]=2)[CH2:12][CH2:13]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
To a solution of 4-(5-bromo-2,3-dihydro-benzofuran-7-yl)-pyridine in toluene was added benzyl bromide (1 eq.) and the reaction mixture was stirred under reflux for 14 h. Reaction was monitored by TLC (CH2Cl2/MeOH 95:5) and revealed total conversion to an intermediate. Complete evaporation of the solvent gave a white solid. The solid was dissolved in MeOH under argon and cooled down to 0° C., NaBH4 (2.05 eq.) was added portion-wise (exothermic reaction) and the reaction mixture was stirred for 3 h at RT. Evaporation of MeOH, redissolution in CH2Cl2 and sequential washing with 1N NaHCO3 and brine, followed by purification by SiO2 gel chromatography (CH2Cl2/MeOH: 98/2) gave 71% yield of the tide compound.
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