[H-].[Na+].[F:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[C:10]1[C:11]2[S:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][C:12]=2[NH:13][CH:14]=1.Br[CH2:23][C:24]([O:26][CH3:27])=[O:25]>CN(C=O)C>[F:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[C:10]1[C:11]2[S:17][C:16]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][C:12]=2[N:13]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:14]=160% NaH in mineral oil (2 eq.) was added at RT to a 0.25M solution of methyl 6-(2-fluorocyclohexyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate in dry DMF, after few min methyl bromoacetate (3 eq.) was added and the mixture was stirred at 60° C. for 1 h and left overnight at RT. After dilution with EtOAc, the organic layer was washed with 1N HCl, sat. NaHCO3 and brine, dried over Na2SO4 and concentrated. Chromatography (PE/EtOAc) afforded the title compound (53%). 1H-NMR (400 MHz, CDCl3, 300K, δ) 7.60 (s, 1H), 6.92 (s, 1H), 4.74 (s, 2H), 4.50 (dtd, 1H, J 48.9, 10.3, 4.5), 3.88 (s, 3H), 3.77 (s, 3H), 2.85-2.76 (m, 1H), 2.25-2.11 (m, 2H), 1.90-1.74 (m, 2H), 1.68-1.54 (m, 2H), 1.44-1.33 (m, 2H); MS (ES+) m/z 354 (M+H)+.
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