[OH:1][CH2:2][C:3]1[S:11][C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[Cl:12])[CH:4]=1.Cl.Cl[CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[OH-].[Na+].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1.[Cl-].[Na+].O.C(OCC)(=O)C>[Cl:12][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[CH:4]=[C:3]([CH2:2][O:1][CH2:15][CH2:16][N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)[S:11][C:10]=12A mixture of 2-(hydroxymethyl)-7-chlorothieno[3,2-b]pyridine 114a (0.35 g, 1.8 mmole), 1-(2-chloro-ethyl)-pyrrolidine hydrochloride (31 g, 18 mmole), benzyltriethylammonium bromide (0.2 g, 0.7 mmole) and 19 M sodium hydroxide (10 mL) in toluene was refluxed for three hours. The reaction mixture was buffered with 50% saturated sodium bicarbonate and the workup was performed with ethyl acetate, brine and magnesium sulfate. The crude product was purified over silica gel (100 g) using 2–7% methanol-chloroform with 0.1% ammonium hydroxide, which provided the title compound as an amber oil (0.38 g, 62%): 1H-NMR (DMSO-d6, 400 MHz) δ 8.62 (1H, d, J=5.0 Hz), 7.58 (1H, s), 7.54 (1H, d, J=5.1 Hz), 4.86 (2H, s), 3.62 (2H, t, J=6.0 Hz), 2.64 (2H, t, J=5.8 Hz), 2.49–2.47 (4H, m), 1.67–1.63 (4H, m); MS m/z 297 (M+H)+.
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