2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → 6-({2-[(3,5-Dimethylphenyl)amino][1,2,4]triazolo[1,5-a]pyrazin-8-yl}amino)-2,2-difluoro-2H-1,4-benzoxazin-3(4H)-one

Participants

Reaction Steps

8-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl-(3,5-dimethyl-phenyl)-amine (0.075 g, 0.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.01 g, 0.01 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (0.01 g, 0.02 mmol) and 6-amino-2,2-difluoro-2H-1,4-benzoxazin-3(4H)-one (0.049 g, 0.2 mmol) are taken in dry 1,4 dioxane (2 mL). Sodiumhexamethyldiisilylamide (1 M in tetrahydrofuran) (0.27 mL, 0.2 mmol) is added and the reaction irradiated in the microwave at 150° C. for 30 minutes. The reaction mixture is quenched with dry methanol (1 mL) and passed through a celite pad. The filtrate is concentrated and purified by flash column chromatography using Silica gel (230-400) mesh to get the titled product as an off white solid (10 mg, 10.4%). TLC: pet ether/ethylacetate (6/4) Rf-0.4. LCMS (method A): mass found (M+H+, 438), Rt (min): 5.11 area % 93.7 (max), 94.4 (254 nm); 1H NMR (400 MHz, DMSO-d6): δ [ppm] 11.99 (s, 1H), 9.63 (s, 1H), 9.39 (s, 1H), 8.27 (d, J=4.48 Hz, 1H), 7.93 (d, J=2.44 Hz, 1H), 7.63 (m, 1H), 7.57 (d, J=4.48 Hz, 1H), 7.35 (s, 2H), 7.27 (d, J=8.92 Hz, 1H), 6.55 (s, 1H), 2.25 (s, 6H).

Provenance & Evidence