Sodium t-butoxide → HCID 59631438, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,5-bis(2-methoxyphenyl)-3-pyridinamine (37.5 mg, 0.12 mmol), 4-chloro-5,7-difluoro-3-methyl-2-(2-pyridinyl)quinoline (54.7 mg, 0.19 mmol), 2-dicyclohexylphosphino-2,4,6,-triisopropylbiphenyl (12.1 mg, 0.025 mmol), tris(dibenzylideneacetone)dipalladium (0) (11.9 mg, 0.013 mmol), and sodium tert-butoxide (36.7 mg, 0.38 mmol) in dry toluene (2.0 mL) was degassed by nitrogen. The mixture was heated to 90° C. After 21.5 h, the reaction was cooled to rt, then treated with water. After extracting twice with EtOAc, the organic layers were combined and dried over anhydrous magnesium sulfate. After filtration and concentration the residue was purified on basic alumina (0-30% EtOAc in hexanes) to afford an impure light yellow film. The film was further purified by HPLC (10-90% of 0.1% TFA acetonitrile solution in 0.1% TFA water solution.) The desired fractions were concentrated then diluted with EtOAc. After washing twice with satd aq. sodium bicarbonate solution and once with brine, the solvent was removed under reduced pressure to yield a white solid as N-(2,5-bis(2-methoxyphenyl)-3-pyridinyl)-5,7-difluoro-3-methyl-2-(2-pyridinyl)-4-quinolinamine. 1H NMR (500 MHz, CDCl3) δ ppm 8.69 (1H, d, J=4.6 Hz), 8.52 (1H, d, J=1.7 Hz), 7.84 (1H, td, J=7.7, 1.7 Hz), 7.76 (1H, d, J=7.6 Hz), 7.62 (2H, m), 7.50 (1H, m), 7.41 (4H, m), 7.16 (1H, t, J=7.5 Hz), 7.08 (1H, d, J=8.1 Hz), 7.04 (3H, m), 3.98 (3H, s), 3.83 (3H, s), 2.06 (3H, br. s.). Mass Spectrum ESI (pos.) m/e: 561.3 (M+1).

Provenance & Evidence