6-Methyl-1,2,3,4-tetrahydroquinoline → [2-(2,5-Dichloro-phenoxy)-pyridin-3-yl]-(6-methyl-3,4-dihydro-2H-quinolin-1-yl)-methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2,5-dichloro-phenoxy)-nicotinic acid (42.6 mg, 0.15 mmol, 1.0 equiv) in anhydrous DMF (1 mL) was added 6-methyl-1,2,3,4-tetrahydro-quinoline (26.5 mg, 0.18 mmol, 1.2 equiv; [CAS RN 91-61-2]), N-ethyldiisopropylamine (97.0 mg, 131 μL, 0.75 mmol, 5.0 equiv; [CAS RN 7087-68-5]) and HATU (68.4 mg, 0.18 mmol, 1.2 equiv; [CAS RN 148893-10-1]). The reaction mixture was heated by microwave irradiation to 100° C. for 10 min. Removal of the solvent mixture under reduced pressure and purification by preparative (Xterra® PrepMSC 18, 5 μm, 19×50 mm column equipped with a Gilson Liquid Handler 215 autosampler, two Rainin Dynamax® SD-300 pumps, a Sedex ELSD 75 lightscatter and a Dionex UVD 340S UV detector) on reversed phase eluting with a gradient of acetonitrile/water provided 30 mg (49%) of the title compound. MS (ISP): 413.2 [M+H]+.

Provenance & Evidence