Triacetoxyperiodinane → (5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)((3R)-3-(dibenzylamino)cyclopentyl)methanone

Participants

Reaction Conditions

Reaction Steps

A solution of (5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)((3R)-3-(dibenzylamino)cyclopentyl)methanol (1.14 g, 1.89 mmol) in DCM (50 mL) was cooled to about 0° C. Dess-Martin periodinane (2.41 g, 5.68 mmol) was added and the reaction mixture was stirred at about 0-10° C. for about 3 h. The mixture was quenched by a drop-wise addition of aqueous sodium sulfite (1 M, 20 mL), and the organic solvent was removed under reduced pressure. The aqueous layer was extracted with EtOAc (2×25 mL), and the combined organic extracts were washed with aqueous NaOH (1 N, 3×20 mL), brine, dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of 0-20% EtOAc in heptane to yield (5-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)((3R)-3-(dibenzylamino)cyclopentyl)methanone (0.68 g, 60%) as a yellow amorphous solid: LC/MS (Table 2, Method a) Rt=1.65 min; MS m/z: 442 (M+H)+.

Provenance & Evidence