5-Ethylsulphonyl-o-anisidine → HCID 86608154, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 7-(3-bromophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (Example 9) (49.1 mg, 0.104 mmol), 5-(ethylsulfonyl)-2-methoxyaniline (22.5 mg, 0.104 mmol), 2-(dit-butylphosphino)biphenyl (16.3 mg, 0.054 mmol), Tris(dibenzylidineacetone)dipalladium (0) (16.6 mg, 0.018 mmol) and sodium t-butoxide (26.0 mg, 0.28 mmol) was added 1,4-dioxane (1.0 mL). In a sealed reaction vessel, the mixture was heated with microwave radiation at 130° C. for 50 minutes. After cooling to room temperature, removed solvent under reduced pressure and diluted residue in dichloromethane. Filtered and added silica gel (500 mg) to filtrate followed by evaporation of the volatiles under reduced pressure. The pre-adsorbed solids were loaded into a solid loading cartridge and subjected to a gradient elution using ethyl acetate:hexanes (25:75) to ethyl acetate:hexanes (95:5) using a RediSep silica gel cartridge (4.2 g; ISCO). The appropriate fractions were combined and concentrated under reduced pressure to give 7-(3-{[5-ethylsulfonyl)-2-methoxyphenyl]amino}phenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo-[5,1-f][1,2,4]triazin-2-amine (0.0195 g) as a yellow solid. 1H NMR (CDCl3): δ8.82 (s, 1H), 8.39 (s, 1H), 8.17 (d, J=7.7 Hz, 1H), 7.82 (s, 1H), 7.42-7.19 (m, 4H), 6.97 (d, J=7.3 Hz, 1H), 6.88 (s, 2H), 6.45 (s, 1H) 4.00 (s, 3H) 3.84 (s, 9H), 3.06 (d, J=6.6 Hz, 2H), 2.60 (s, 3H), 1.25 (m, 3H). MS m/z 605 (M+1).

Provenance & Evidence