C([Si](C)(C)[N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[CH:8]=[CH:7]1)(C)(C)C.[CH3:17][C:18]1([CH3:26])[O:25][C:23](=[O:24])[CH2:22][C:20](=[O:21])[O:19]1.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.N1CCC[C@H]1C(O)=O>C(#N)C>[CH3:17][C:18]1([CH3:26])[O:25][C:23](=[O:24])[CH:22]([CH:27]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:8]2[C:9]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:6][CH:7]=2)[C:20](=[O:21])[O:19]1To a room temperature (RT) solution of 1-(tert-butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine (Synthesis 1999, 615-620) (2.88 g, 9.47 mmol) in acetonitrile (20 ml) was added Meldrum's acid (1.5 g, 10 mmol), benzaldeyde (1.9 ml, 19 mmol) triethylamine (TEA) (1.9 ml, 14 mmol) and proline (catalytic quantity). The mixture was stirred overnight at RT, concentrated, and the residue was partitioned between EtOAc and brine. The aqueous layer was extracted twice with EtOAc. The organic layers were combined, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc), affording 2,2-dimethyl-5-[phenyl-(1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-[1,3]dioxane-4,6-dione.
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