Ethyl bromodifluoroacetate → (S)-Ethyl 2,2-difluoro-2-(2'-oxo-1'-((2-(trimethylsilyl)ethoxy)methyl)-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-3-yl)acetate

Participants

Reaction Conditions

Reaction Steps

Copper bronze (0.522 g, 8.22 mmol) was added to a solution of (S)-3-iodo-1′-((2-(trimethylsilyl)ethoxy)methyl)-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-2′(1H)-one (described in Intermediate 7) (0.811 g, 1.644 mmol) and ethyl bromodifluoroacetate (1.056 mL, 8.22 mmol) in DMSO (10 mL) at ambient temperature. The resulting mixture was heated to 100° C. and stirred for 4 h. The reaction was cooled, partitioned between water (40 mL) and EtOAc (200 mL). The organic layer was removed and the aqueous phase was extracted further with EtOAc (30 mL). The combined organic extracts were washed with brine, then dried over sodium sulfate, filtered, and concentrated to dryness in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexanes:EtOAc—85:15 to 0:100, to give the title compound. MS: m/z=489.1 (M+1).

Provenance & Evidence