Dimethylformamide → 2-dimethylaminomethyl-1H-indole-5-carbaldehyde

To a cold (0° C.) solution of potassium hydride (suspension in mineral oil, 0.79 g, 5.90 mmol) in anhydrous THF (60 mL) was added a solution of (5-bromo-1H-indole-2-ylmethyl)-dimethyl amine (1.24 g, 4.90 mmol) in anhydrous THF (20 mL) was added dropwise at 0° C. over a period of 15 minutes under nitrogen. Stirring was continued for 30 minutes at 0° C., then cooled to −10° C. n-Butyl lithium (1.6 M solution in hexanes, 7.4 mL, 11.7 mmol) was added rapidly. Stirring was continued at −10° C. for 1 h. Then, anhydrous DMF (5.0 mL) was added, and the mixture was allowed to warm to room temperature over 2 h. The reaction mixture was carefully quenched with 1N aq. HCl (10 mL). The reaction mixture was diluted with ethyl acetate (150 mL). The organic phase was separated, washed with water (100 mL), then brine (100 mL), and dried over anhydrous Na2SO4. The solvent was evaporated to give 2-dimethylaminomethyl-1H-indole-5-carbaldehyde as an orange-colored gummy material. Yield: 0.91 g (crude). This product was used in next step without further purification.

1. additionwas added dropwise at 0° C. over a period of 15 minutes under nitrogen
2. additionwas added rapidly
3. stirringStirring
4. waitwas continued at −10° C. for 1 h
5. customThe reaction mixture was carefully quenched with 1N aq. HCl (10 mL)
6. additionThe reaction mixture was diluted with ethyl acetate (150 mL)
7. customThe organic phase was separated
8. washwashed with water (100 mL)
9. dry with materialbrine (100 mL), and dried over anhydrous Na2SO4
10. customThe solvent was evaporated

ORD record

ord-125e1493e4d04a1eb8a68fb41a98bfba

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238640B2