O[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.[CH2:13]([N:15](CC)[CH2:16][CH3:17])[CH3:14].S(Cl)(C)(=O)=O.N1CCCC1.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>ClC(Cl)C.[Cl-].[Na+].O.ClCCl>[Cl:12][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[CH:4]=[C:3]([CH2:2][N:15]3[CH2:16][CH2:17][CH2:14][CH2:13]3)[S:11][C:10]=12A solution of 2-(hydroxymethyl)-7-chlorothieno[3,2-b]pyridine 114a (100 mg, 0.5 mmole) in dichloroethane was treated with triethylamine (0.08 mL, 0.55 mmole) and mesyl chloride (0.04 mL, 0.55 mmole). The clear solution was stirred for 30 minutes and treated with pyrrolidine (0.12 mL, 1.5 mmole). After one hour, the reaction mixture was poured into 5% sodium bicarbonate and the workup was performed with dichloromethane, brine and magnesium sulfate. The crude product (167 mg greenish oil) was purified over silica gel (1 mm plate) using 2% methanol-chloroform with 0.1% ammonium hydroxide, which provided the title compound as a clear oil (71 mg, 56%): 1H-NMR (DMSO-d6, 400 MHz) δ 8.58 (1H, d, J=5.1 Hz), 7.51–7.49 (2H, m), 3.96 (2H, s), 2.56 (4H, bs), 1.75–1.72 (4H, m); MS m/z 253 (M+H)+.
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