Triacetoxyperiodinane → (5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)(cyclobutyl)methanone
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[C:25]([CH:33]([CH:35]2[CH2:38][CH2:37][CH2:36]2)[OH:34])=[C:26]2[CH:32]=[CH:31][NH:30][C:27]2=[N:28][CH:29]=1>C(Cl)Cl>[Cl:23][C:24]1[C:25]([C:33]([CH:35]2[CH2:36][CH2:37][CH2:38]2)=[O:34])=[C:26]2[CH:32]=[CH:31][NH:30][C:27]2=[N:28][CH:29]=1Participants
4
Procedure
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)+.