Diisopropylethylamine → [2-(2,5-Dichloro-phenoxy)-pyridin-3-yl]-(2,3,3a,4-tetrahydro-1H-pyrrolo[1,2-a]quinoxalin-5-yl)-methanone

Participants

Reaction Steps

To a solution of 4,5-dihydro-pyrrolo[1,2-α]quinoxaline (30.6 mg, 0.18 mmol, 1.2 equiv; [CAS RN 56721-86-9]) in ethanol (5 mL) was added palladium on carbon (3.2 mg, 0.003 mmol, 0.02 equiv; 10% Pd/C; [CAS RN 7440-05-3]) and the reaction mixture stirred under an atmosphere of hydrogen (3 bar) at rt for 4 h. The reaction mixture was concentrated under reduced pressure, filtered over Celite® and the remaining residue redissolved in anhydrous DMF (1 mL). To this solution was added N-ethyldiisopropylamine (64 mg, 86 μL, 0.50 mmol, 5.0 equiv; [CAS RN 7087-68-5]) and 2-(2,5-dichloro-phenoxy)-nicotinoylchloride (45.4 mg, 0.15 mmol, 1.0 equiv; prepared according to Example 122) and the reaction mixture stirred at rt over night. Removal of the solvent mixture under reduced pressure and purification by preparative HPLC on reversed phase (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) eluting with a gradient of acetonitrile/water provided 21.4 mg (32%) of the title compound. MS (ISP): 440.1 [M+H]+.

Provenance & Evidence