p-Toluenesulfonic acid monohydrate → N-(4-bromo-2-methoxy-5-nitrophenyl)-4-(1-methylindol-3-yl)pyrimidin-2-amine

Participants

Reaction Steps

A solution of 3-(2-chloropyrimidin-4-yl)-1-methylindole (Intermediate 130, 0.829 g, 3.40 mmol), p-toluene sulphonic acid monohydrate (0.924 g, 4.86 mmol) and 4-bromo-2-methoxy-5-nitroaniline (Intermediate 4, 0.8 g, 3.24 mmol) was heated at reflux in 2-pentanol (32 mL) under an atmosphere of N2 for 18 h. The mixture was then allowed to cool, and was then concentrated in vacuo. The resulting residue was triturated with CH3CN until a yellow precipitate formed. This solid was collected by filtration and was washed with diethyl ether. The solid was suspended in 10% CH3OH in CH2Cl2 and washed with saturated aqueous NaHCO3 (2×) followed by water. The organic solution was then concentrated in vacuo, and the resulting residue was triturated in CH3CN/water. The mixture was then filtered, and the collected solid was washed with CH3CN followed by diethyl ether and was then air dried to give the title compound (1.082 g, 74%) as a yellow solid; 1H NMR: 3.90 (3H, s), 4.05 (3H, s), 7.15-7.21 (1H, m), 7.26-7.31 (1H, m), 7.36 (1H, d), 7.52 (1H, s), 7.56 (1H, d), 8.34 (1H, s), 8.39 (1H, s), 8.40-8.45 (2H, m), 9.20 (1H, s); m/z: ES+ MH+ 454/456.

Provenance & Evidence