1,8-Diazabicyclo(5.4.0)undec-7-ene → (S)-tert-butyl 2-(9H-pyrido[2,3-b]indol-6-yl)morpholine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

(S)-tert-Butyl 2-(4-(3-chloropyridin-2-ylamino)phenyl)morpholine-4-carboxylate (47 mg, 0.12 mmol), palladium(II)-acetate (2.7 mg, 0.012 mmol), tricyclohexylphosphine tetrafluoroborate (9 mg, 0.024 mmol) and DBU (37 mg, 0.24 mmol) were dissolved in a mixture of o-xylene (0.7 ml) and dimethylacetamide (0.7 ml). The mixture was degassed with argon for 5 min and heated at 155° C. for 16 h in a closed vial. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over MgSO4 and evaporated. Flash chromatography (2 g silica gel, 10 to 30% ethyl acetate in heptane) yielded a white solid (22 mg, 52%), MS (ISP): 354.3 ([M+H]+).

Provenance & Evidence