2-(Dimethylamino)ethanol → tert-butyl 6-(2-(dimethylamino)ethoxy)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl-6-iodo-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (500 mg, 1.26 mmol), copper(I) iodide (71.7 mg, 0.38 mmol) and tri-potassium orthophosphate (533 mg, 2.51 mmol) were suspended in 2-dimethylaminoethanol (10 ml, 99.40 mmol) and sealed into a microwave tube. The reaction was heated to 150° C. for 1 hour in the microwave reactor and cooled to RT. The reaction mixture was diluted with DCM (100 mL), and washed with 2N NaOH (3×50 mL). The organic layer was dried over Na2SO4, filtered and evaporated to afford crude product. The crude product was purified by preparative HPLC (0.1% NH3, CH3CN/H2O gradient) to afford tert-butyl 6-(2-(dimethylamino)ethoxy)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (304 mg, 67%) as a yellow gum.

Provenance & Evidence