Trifluoroacetic acid → (2-(2-Amino-3-(2-ethylmorpholino)quinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone

Participants

Reaction Conditions

Reaction Steps

A mixture of (2-bromo-3-methylphenyl)(pyrrolidin-1-yl)methanone (0.256 g, 0.953 mmol), 3-(2-ethylmorpholino)-N-(4-methoxybenzyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.16 g, 0.318 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′,-tri-1-propyl-1,1′-biphenyl (0.030 g, 0.064 mmol), potassium phosphate, anhydrous (0.132 mL, 1.589 mmol), and Pd2(dba)3 (0.029 g, 0.032 mmol) was purged with N2 followed by the addition of degassed dioxane (2 mL) and degassed water (1.0 mL). The resulting mixture was heated in microwave at 140° C. for 12 min. The reaction went to completion and it was filtered, concentrated, and chromatographed on silica gel using 0-5% MeOH/DCM to afford a light yellow oil. To this product was added TFA (15 mL, 195 mmol) and heated at 70° C. for 18 h until the starting material was consumed. The mixture was concentrated and chromatographed on silica gel using 0-5% 2M NH3 in MeOH/DCM to afford a light yellow solid as (2-(2-amino-3-(2-ethylmorpholino)quinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone. MS (ESI, pos. ion) m/z: 445 (M+1).

Provenance & Evidence