Dimethylformamide → (2E)-3-[4-(tert-Butyl)phenyl]-N-(1-methylindol-5-yl)prop-2-enamide

1-Methylindole-5-ylamine. To a round-bottomed flask was added 5-nitroindole (0.81 g, 5.0 mmol, Aldrich) and anhydrous DMF (40 mL). The solution was stirred magnetically and treated with sodium hydride (0.40 g, 10 mmol, 60% dispersion in mineral oil, Aldrich) followed by iodomethane (0.71 gm 10 mmol, Aldrich). Stirring was continued at 25° C. for 30 min, then the reaction mixture was quenched by the addition of water (75 mL) and extracted with EtOAc. The organic extract was concentrated in vacuo to provide a crude residue. Analogous to the procedure of Goswami, P.; Chowdhury, P.; Indian J Chem, Sect B, 1997, 36 (2), 185-186, the crude residue was dissolved in THF (40 mL) and added to Zn dust (0.22 g, 3.3 mmol, Aldrich) and AlCl3.6H2O (4.78 g, 19.8 mmol, Aldrich) in water (1 mL), magnetically stirred at 25° C. The reaction mixture was stirred at 25° C. for 16 h, then filtered. The filtrate was added to cold water (300 mL) and extracted with CH2Cl2 (3×100 mL). The combined organic extract was concentrated in vacuo to provide the title product. MS (ESI, pos. ion) m/z: 147 (M+1).

1. stirringStirring
2. customthe reaction mixture was quenched by the addition of water (75 mL)
3. extractionextracted with EtOAc
4. extractionThe organic extract
5. concentrationwas concentrated in vacuo
6. customto provide a crude residue
7. stirringmagnetically stirred at 25° C
8. stirringThe reaction mixture was stirred at 25° C. for 16 h
9. filtrationfiltered
10. additionThe filtrate was added to cold water (300 mL)
11. extractionextracted with CH2Cl2 (3×100 mL)
12. extractionThe combined organic extract
13. concentrationwas concentrated in vacuo

ORD record

ord-672d33199fbc4e6c8e4341c489c2fb63

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07579347B2