反应详情

温度

100 °C

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).

1. temperatureThe reaction was cooled
2. custompartitioned between water (40 mL) and EtOAc (200 mL)
3. customThe organic layer was removed
4. extractionthe aqueous phase was extracted further with EtOAc (30 mL)
5. washThe combined organic extracts were washed with brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated to dryness in vacuo
9. customThe crude product was purified by silica gel chromatography
10. washeluting with a gradient of hexanes