P,P,P′,P′-Tetraethyl P,P′-ethylidenebis[phosphonate] → HCID 131731110, compound

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Reaction Steps

As shown in FIG. 6, 8-Benzyloxy-3-iodo-imidazo[1,2-α]pyridine 31 (Example 20).(7.0 g, 20 mmol) in anhydrous THF (200 mL) was stirred at −78° C., under argon, then n-BuLi (2.5 M, 16.0 mL, 40 mmol) in hexanes was added slowly, keeping the temperature below −70° C. . The resulting mixture was stirred for 10 min, then tetraethyl ethene-1,1-bisphosphonate 3 (6.0 g, 20.0 mmol) in anhydrous THF (20 mL) was added slowly, keeping the temperature below −70° C. The reaction mixture was stirred for an additional 10 minutes, cooled to room temperature, and then quenched with saturated NH4Cl (100 mL). The mixture was then extracted with CH2Cl2 (200 mL×3) and the organic phase washed with water (200 mL×2). The resultant organic phase was then dried with Na2SO4, concentrated under reduced pressure and purified on silica gel (CombiFlash, EtOAc/MeOH elution) to afford [2-(8-Benzyloxy-imidazo[1,2-α]pyridin-3-yl)-1-(diethoxy-phosphoryl)-ethyl]-phosphonic acid diethyl ester 35 as yellowish brown oil. 7.18 g, 69% yield.

Provenance & Evidence