Reaction #1485681

Reaction equation

4-chloro-N-(2-methoxypyridin-3-yl)-1,3,5-triazin-2-amine

6-bromo-1H-indazole

NaH

→

title compound

4-(6-bromo-1H-indazol-1-yl)-N-(2-methoxypyridin-3-yl)-1,3,5-triazin-2-amine

Solvents

DMF

Conditions

Workup

1. 1
   OtherThe reaction mixture was quenched with water and EtOAc
2. 2
   workup.ADDITIONadded
3. 3
   OtherThe resultant precipitate was collected
4. 4
   Otherfurther drying under vacuum

Procedure

To a solution of 6-bromo-1H-indazole (172 mg, 0.87 mmol) in DMF (8 mL) was added NaH (60% in oil, 69.8 mg, 1.75 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 10 minutes before the addition of 4-chloro-N-(2-methoxypyridin-3-yl)-1,3,5-triazin-2-amine (311.18 mg, 1.31 mmol). Stirring was continued at RT for 2 hr. The reaction mixture was quenched with water and EtOAc added. The resultant precipitate was collected and further drying under vacuum gave the title compound as a beige solid; 1H NMR (250 MHz, CDCl3) δ 4.09 (3H, s), 7.05 (1H, d, J=2.28 Hz), 7.50 (1H, dd, J=8.53, 1.68 Hz), 7.62-7.70 (1H, m), 7.88-8.09 (2H, m), 8.30 (1H, d, J=0.76 Hz), 8.74 (1H, dd, J=7.77, 1.68 Hz), 8.83 (1H, s), 9.01 (1H, s); LC-MS: m/z=+397.9/399.8 (M+H)+.

Source