1,2-Dimethoxyethane → HCID 11156498, 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) (25 mg, 0.05 mmol), 3-(dihydroxyboryl)benzoic acid (10.6 mg, 0.06 mmol), tetrakis(triphenylphosphine) palladium (0) (3.1 mg, 0.003 mmol) and potassium carbonate (11.0 mg, 0.08 mmol) was added DME (0.9 mL) and distilled water (0.3 mL). In a sealed reaction vessel, the mixture was heated with microwave radiation at 110° C. for 20 minutes. After cooling to room temperature, removed solvent under reduced pressure, dissolved residue in dichloromethane and methanol, and added silica gel (200 mg). Following 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 dichloromethane:methanol (100:0) to (80:20) using a RediSep silica gel cartridge (4.2 g; ISCO). The appropriate fractions were combined and concentrated under reduced pressure to give a solid that was suspended in dichloromethane and vacuum filtered to give 3′-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}-1,1′-biphenyl-3-carboxylic acid (0.0164 g) as a yellow solid. 1H NMR (DMSO-d6): δ9.63 (s, 1H), 9.26 (s, 1H), 8.57-8.53 (m, 2H), 8.21 (s, 1H), 7.95-7.92 (m, 2H), 7.78 (d, J=6.2 Hz, 1H), 7.62-7.55 (m, 2H), 7.07 (s, 2H), 3.63 (s, 6H), 3.58 (s, 3H), 2.55 (s, 3H). MS m/z 512 (M+1).

Provenance & Evidence