Benzyl Bromide → 5-benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

To a stirred solution of the crude stannane 17 (172 mg, 0.33 mmol) in THF (2.5 mL) was added PhCH2Br (0.03 mL, 0.27 mmol) and (Ph3P)2PdCl2 (5 mg, 0.007 mmol). The mixture was refluxed under N2 for 19 h, cooled, and partitioned between AcOEt-brine. The aqueous layer was extracted with AcOEt (2×). The combined organic solutions were dried (MgSO4), and concentrated in vacuum. The residual yellow oil was dissolved in MeOH (3 mL) and treated with a 10% solution of HCl in MeOH (2 mL). The mixture was stirred for 2.5 h, neutralized with saturated aqueous NaHCO3 solution and extracted with AcOEt (2×). The combined organic extracts were dried (MgSO4), concentrated, and purified by PTLC with CH2Cl2:MeOH=95:5 as eluent to afford the 5-benzyl derivative 18 (8 mg, 11% over 2 steps). 1H NMR (400 MHz; CDCl3) δ 2.99 (t, J=8.1 Hz, 2H), 3.60 (t, J=8.3 Hz, 2H), 3.79 (s, 2H), 7.06-7.31 (m, 7H), 7.69 (br s, NH).

Provenance & Evidence