Acetic Acid → HCID 19900476, compound

Participants

Reaction Steps

To a solution of 1-(propyl-4-pyridinylamino)-1H-indol-5-ol (2.5 g) in 40 ml of tetrahydrofuran was added 1,1'-carbonyldiimidazole (1.83 g) and this mixture was stirred for 24 hours. Then 3.5 ml of glacial acetic acid was added to the reaction mixture. Then 1,2,3,4-tetrahydroisoquinoline (1.49 g) in 10 ml of tetrahydrofuran which had been acidified with 0.60 ml of glacial acetic acid was added to the reaction mixture dropwise. This was stirred for 24 hours and then the reaction mixture was quenched with water, basified with saturated sodium carbonate solution and extracted with ethyl acetate. The organic layer was washed with water and dried (sat. NaCl, anhy. MgSO4). After filtration, the solvent was evaporated to yield an oil (5.6 g) which was eluted with 5% methanol/dichloromethane on a silica gel column via HPLC. The desired fractions were concentrated to yield an oil (4.2 g). This material was dissolved in pentane/ether (1:1), whereupon a solid precipitated out of the solution. This material was collected to yield a solid, 2.6 g, m.p. 141°-143° C.

Provenance & Evidence