Sodium Carbonate → 5-chloro-4-(1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-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 (68.7 mg, 0.14 mmol) (described herein), 4,5-dichloropyrimidin-2-amine (22.1 mg, 0.14 mmol), bis(triphenylphosphine)palladium(ii) chloride (9.5 mg, 0.013 mmol), and sodium carbonate (42.9 mg, 0.41 mmol) in 1,4-dioxane (2.9 mL) and water (0.73 mL), and heating in a microwave at 120° C. for 60 min. After purification 5-chloro-4-(1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-2-pyrimidinamine was obtained as a yellow solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.74 (1H, dd, J=3.9, 1.2 Hz), 8.19 (1H, s), 7.76-7.99 (4H, m), 7.35-7.42 (1H, m), 7.28-7.30 (1H, m), 7.23-7.27 (1H, m), 7.16 (1H, dd, J=7.4, 1.2 Hz), 6.36 (1H, s), 4.94-5.21 (2H, br. s.), 3.76-3.88 (2H, m), 2.37 (3H, s), 1.58 (3H, s), 1.52 (3H, s). Mass Spectrum (ESI) m/e=511 (M+1).

Provenance & Evidence