Sodium Carbonate → 4-(1-(7-Fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-6-methyl-2-pyrimidinamine

Participants

Reaction Conditions

Reaction Steps

Prepared according to procedure P using 4-(3,3-dimethyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-1-yl)-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (70 mg, 0.14 mmol) (described herein), 4-chloro-6-methylpyrimidin-2-amine (21.7 mg, 0.15 mmol), bis(triphenylphosphine)palladium(ii) chloride (9.6 mg, 0.014 mmol), and sodium carbonate (43.7 mg, 0.41 mmol) in 1,4-dioxane (3.1 mL) and water (0.79 mL), and heating in a microwave at 120° C. for 60 min. After purification 4-(1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-6-methyl-2-pyrimidinamine was obtained as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.75 (1H, d, J=4.3 Hz), 7.76-7.96 (4H, m), 7.34-7.46 (2H, m), 7.28 (1H, br. s.), 7.21-7.26 (1H, m), 6.66-6.76 (1H, m), 6.58 (1H, d, J=1.2 Hz), 5.19 (2H, br. s.), 3.74-3.90 (2H, m), 2.35-2.41 (3H, m), 2.28-2.35 (3H, m), 1.55-1.61 (3H, m), 1.49-1.55 (3H, m). Mass Spectrum (ESI) m/e=491 (M+1).

Provenance & Evidence