Dimethylformamide → [2-(2,5-Dichloro-phenoxy)-5-fluoro-pyridin-3-yl]-(4-furan-3-ylmethyl-3,4-dihydro-2H-quinoxalin-1-yl)-methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of [2-(2,5-dichloro-phenoxy)-5-fluoro-pyridin-3-yl]-(3,4-dihydro-2H-quinoxalin-1-yl)-methanone (25.1 mg, 0.06 mmol, 1.0 equiv; Example 148) in anhydrous DMF (1 mL) was added furan-3-carbaldehyde (23.1 mg, 20 μL, 0.24 mmol, 4.0 equiv; [CAS RN 498-60-2]), dibutyltin dichloride (1.8 mg, 0.006 mmol, 0.1 equiv; [CAS RN 683-18-1]) and phenylsilane (13.0 mg, 15 μL, 0.12 mmol, 2.0 equiv; [CAS RN 694-53-1]). The reaction mixture was heated by microwave irradiation to 150° C. for 15 min. 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 5.4 mg (18%) of the title compound as a light yellow solid. MS (ISP): 498.3 [M+H]+.

Provenance & Evidence