Diisopropylethylamine → [2-(4-Bromo-2,5-dichloro-phenoxy)-pyridin-3-yl]-(4-cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)-methanone

Participants

Reaction Steps

To a solution of 2-(4-bromo-2,5-dichloro-phenoxy)-nicotinic acid (50 mg, 0.14 mmol, 1.0 equiv) in anhydrous dichloromethane (1.5 mL) was added N-ethyldiisopropylamine (36 mg, 47 μL, 0.28 mmol, 2.0 equiv; [CAS RN 7087-68-5]) and HATU (68 mg, 0.18 mmol, 1.3 equiv; [CAS RN 148893-10-1]) and the reaction mixture stirred at rt. After 10 min, 1-cyclopropyl-1,2,3,4-tetrahydro-quinoxaline (29 mg, 0.17 mmol, 1.2 equiv; Example 125, Step 5) was added and stirring at rt continued over night. To the reaction was added a sat. solution of NaHCO3 (20 mL) and the solution extracted with dichloromethane (3×20 mL). The combined organic phases were dried over Na2SO4 and the product purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate affording 45 mg (63%) of the title compound as an off-white powder. MS (ISP): 520.3 [M+H]+.

Provenance & Evidence