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

Dess-Martin periodinane (1.6 g, 3.8 mmol) was added to a suspension of (5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)(cyclobutyl)methanol (0.3 g, 1.2 mmol) in DCM (7 mL) at about 0° C. The reaction mixture was stirred at ambient temperature for about 4 h then quenched by the addition of with saturated aqueous Na2SO3 (125 mL). The product was extracted into DCM (3×20 mL) and the combined organic extracts were washed with aqueous NaOH (2 N, 20 mL). The organic phase was dried over anhydrous MgSO4 and the solvent was removed under reduced pressure to provide (5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)(cyclobutyl)methanone as an off-white solid (0.2 g, 67%) that was used directly in the next step without further purification: LC/MS (Table 2, Method a) Rt=2.27 min; m/z: 235 and 237 (M+H)+.

1. customthen quenched by the addition of with saturated aqueous Na2SO3 (125 mL)
2. extractionThe product was extracted into DCM (3×20 mL)
3. washthe combined organic extracts were washed with aqueous NaOH (2 N, 20 mL)
4. dry with materialThe organic phase was dried over anhydrous MgSO4
5. customthe solvent was removed under reduced pressure

ORD record

ord-e0291d06d2d84cf9be868c7e0315b79f

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365579B2