[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl-].C[Al+]C.[F:11][C:12]1[CH:21]=[CH:20][C:19]2[O:18][CH2:17][C:16]3[CH:22]=[C:23]([C:25]([O-])=[O:26])[S:24][C:15]=3[C:14]=2[CH:13]=1>ClCCCl>[F:11][C:12]1[CH:21]=[CH:20][C:19]2[O:18][CH2:17][C:16]3[CH:22]=[C:23]([C:25]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:26])[S:24][C:15]=3[C:14]=2[CH:13]=1To a cooled solution (ice/H2O) of morpholine in DCE was added slowly dropwise 2 equiv. of dimethylaluminum chloride. This reaction was stirred for greater than 30 minutes until reaching ambient temperature. Next the reaction was again cooled (ice/H2O) and 8-fluoro-4H-thieno[3,2-c]chromene-2-carboxylate was added as a solid portion wise. The reaction was allowed to equilibrate to ambient temp and monitored by LC/MS. The completed reaction was quenched with an aqueous solution of Na, K-tartrate (20% wt/wt). This mixture was extracted with EtOAc and the organic was washed with saline and dried (MgSO4). The dried org. was concentrated in vacuo to a residue. This residue was not soluble in DMF and 170bp as a white solid was collected by vacuum filtration, Yield=40% of theoretical. MS: (ESI+)=320.5
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