Cesium carbonate → 1-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-phenyl]-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-1H-pyridin-4-one

Participants

Reaction Conditions

Reaction Steps

To each of three 20 mL microwave tubes was added 0.5 g (1.2 mmol) 1-(3-bromo-phenyl)-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-1H-pyridin-4-one, 0.33 g (0.45 mmol) dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloromethane adduct, 0.51 g (1.44 mmol) 5-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine, 3.6 mL (3.6 mmol) 1 M aq. Cs2CO3, and 10 mL THF. The vials were then capped and heated by microwave to 150° C. for 12 minutes each. After cooling, the aqueous layer was removed and the organics were concentrated in vacuo. Purification by automated flash chromatography (40 g silica gel cartridge 0-10% MeOH/EtOAc over 30 min) afforded 1-[3-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)-phenyl]-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-1H-pyridin-4-one. LCMS (M+H)+ 488.4.

Provenance & Evidence