Dimethylamine → 5-bromo-1H-indole-2-carboxylic acid dimethylamide

To a solution of 5-bromo-1H-indole-2-carboxylic acid (2.40 g, 10.0 mmol) in THF (100 mL) were added EDCl (2.11 g, 30.0 mmol), HOBt (1.49 g, 11.0 mmol). The reaction mixture was stirred at room temperature for 10 minutes. Then, a solution of N,N-dimethyl amine (2.0 M solution in THF, 15 mL, 30.0 mmol) was added. The mixture was stirred for 16 hours at room temperature. Solvent was evaporated, the residue was taken in ethyl acetate (200 mL), and water (200 mL) was added. The organic phase was separated; the aqueous phase was extracted with ethyl acetate (200 mL). The combined organic phase was washed with water (100 mL), then brine (100 mL), and dried over anhydrous sodium sulfate. Solvent was evaporated and dried under vacuum to give 5-bromo-1H-indole-2-carboxylic acid dimethylamide as an off-white solid. Yield: 2.56 g (96%).

1. stirringThe mixture was stirred for 16 hours at room temperature
2. customSolvent was evaporated
3. additionwater (200 mL) was added
4. customThe organic phase was separated
5. extractionthe aqueous phase was extracted with ethyl acetate (200 mL)
6. washThe combined organic phase was washed with water (100 mL)
7. dry with materialbrine (100 mL), and dried over anhydrous sodium sulfate
8. customSolvent was evaporated
9. customdried under vacuum

ORD record

ord-f0109ed374164b00a365524ac0d1c636

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238640B2