[H-].[Na+].CI.[Cl:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[CH:12]=[C:13]([C:15]([N:17]3[CH2:21][CH2:20][CH:19]([CH2:22][NH:23][C:24](=O)OC(C)(C)C)[CH2:18]3)=[O:16])[S:14][C:7]=12>C1COCC1>[Cl:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[CH:12]=[C:13]([C:15]([N:17]3[CH2:21][CH2:20][CH:19]([CH2:22][NH:23][CH3:24])[CH2:18]3)=[O:16])[S:14][C:7]=12NaH (0.033 g, 0.82 mmole) and CH3I (0.064 ml, 1.02 mmole) were added to a solution of tert-butyl {1-[(7-chlorothieno[3,2-b]pyridin-2-yl)carbonyl]pyrrolidin-3-yl}methyl-carbamate 43 (0.271 g, 0.68 mmole) in THF at 0° C. The reaction mixture was stirred and warmed to room temperature overnight and partitioned between H2O (50 ml) and EtOAc (2×50 ml). The combined organic layers were dried over MgSO4 and concentrated. The residue was purified by flash column chromatography eluting with 0-2% CH3OH in CH2Cl2 to give a yellow solid (0.283 g, 82%). 1H NMR (300 MHz, CDCl3) δ8.62 (1H, d, J=5.1 Hz), 7.85 (1H, s), 7.34 (1H, d, J=5.1 Hz), 4.72 (1H, s), 3.99 (1H, m), 3.77 (2H, m), 3.50 (1H, m), 3.19 (2H, m), 2.88 (3H, d, J=12.06 Hz), 2.62 (1H, m), 2.14 (1H, m), 1.83 (1H, m); ESIMS (MH+): 310.10.
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