1,2,3,4-Tetrahydroisoquinoline → methyl 4-(3,4-dihydro-1H-isoquinolin-2-yl)benzoate

Temperature

100 °C

methyl 4-bromobenzoate (100 mg, 0.47 mmol), [Reactants] and Cesium carbonate (152 mg, 0.47 mmol) were mixed in toluene (4 mL) and degassed by bubbling nitrogen through solution. Palladium acetate (5.22 mg, 0.02 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (20.27 mg, 0.03 mmol) were added and the vial was capped and heated at 100°C over 5 days. Product had formed in mixture. Workup by dilution with EtOAc, washing with water, then extraction with 2M HCl. The HCl extract was neutralized with 2M NaOH and extracted with EtOAc and the EtOAc phase was dried (K2CO3) and evaporated to give the crude product. No product. Discarded.

ORD record

ord-d7ba527a2d2d4d7591368f0e50bee26a

Source dataset

750 AstraZeneca ELN dataset

Original link

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