Formaldehyde → (2E)-3-[4-(tert-Butyl)phenyl]-N-(1-methylindolin-6-yl)prop-2-enamide

Temperature

25 °C

1-Methylindoline-6-ylamine. To a round-bottomed flask was added 6-nitroindoline (1.64 g, 10.0 mmol, Aldrich), 37% aq. formaldehyde (2.35 g, 30.0 mmol, Aldrich) and THF (40 mL). The reaction mixture was magnetically stirred at 25° C. and treated with sodium cyanoborohydride (1.89 g, 30.0 mmol, Aldrich). The reaction mixture was allowed to stir at 25° C. for 30 min, then washed with satd Na2CO3. The aqueous phase was extracted with ethyl ether, the organic phases combined and concentrated in vacuo to a 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 tetrahydrofuran (60 mL) and added to Zn dust (0.43 g, 6.6 mmol, Aldrich) and AlCl3.6H2O (9.6 g, 40 mmol, Aldrich) in water (2 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 as a brown solid. MS (ESI, pos. ion) m/z: 149 (M+1).

1. stirringto stir at 25° C. for 30 min
2. washwashed with satd Na2CO3
3. extractionThe aqueous phase was extracted with ethyl ether
4. concentrationconcentrated in vacuo to a residue
5. dissolutionIndian J Chem, Sect B, 1997, 36 (2), 185-186, the crude residue was dissolved in tetrahydrofuran (60 mL)
6. stirringmagnetically stirred at 25° C
7. stirringThe reaction mixture was stirred at 25° C. for 16 h
8. filtrationfiltered
9. additionThe filtrate was added to cold water (300 mL)
10. extractionextracted with CH2Cl2 (3×100 mL)
11. extractionThe combined organic extract
12. concentrationwas concentrated in vacuo

ORD record

ord-60e8e49f2bc5411d8bf85588256d7cab

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582657B2