Triacetoxyperiodinane → HCID 58010041, compound

Participants

Reaction Steps

To a suspension of (5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)(cyclohexyl)methanol (1.97 g, 7.44 mmol) in DCM (39.4 mL) at about 0° C. was added Dess-Martin periodinane (9.47 g, 22.3 mmol). The reaction mixture was stirred at ambient temperature for about 4 h then quenched by the addition of saturated aqueous Na2SO3 (125 mL). To control the resulting exothermic reaction, the reaction flask was cooled down in an ice bath during the addition. The product was extracted into DCM (3×40 mL) and the combined organic extracts were washed with aqueous NaOH (2 N, 100 mL). The organic phase was dried over anhydrous MgSO4, filtered, and the solvent was removed under reduced pressure to provide (5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)(cyclohexyl)methanone as an off-white solid (1.75 g, 90%); LC/MS (Table 2, Method a) Rt=2.61 min; MS m/z: 263 and 265 (M+H)+. The material was used directly in the next step without further purification.

Provenance & Evidence