Dimethyl methylphosphonate → [6-(2,3-Dihydro-1H-pyrrolo [2,3-b]pyridin-6-yl)-2-oxo-hexyl]-phosphonic acid dimethyl ester

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Reaction Steps

A solution of dimethyl methylphosphonate (1.35 g, 10.9 mmol) in anhydrous THF (20 mL) was cooled to −78° and treated dropwise with 2.6 M n-BuLi (4.1 mL). After stirring at −78° for 15 min, a solution of ester 23-6 (0.750 g, 2.71 mmol) in THF (10 mL) was added dropwise and the resulting solution stirred for 15 min at −78°, quenched with sat. NH4Cl (25 mL), then extracted with CHCl3 (1×25 mL), and the organic layer was applied to PCTLC (4 mm, 10% MeOH/CHCl3) affording 0.79 g (89% yield) of 23-7.

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