6-AMINO-3,3-DIMETHYL-2-OXO-1,3-DIHYDRO-INDOLE Chemical Properties

Boiling point:

366.6±42.0 °C(Predicted)

Density 

1.161±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

14.32±0.40(Predicted)

Appearance

Dark brown to black Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

6-AMINO-3,3-DIMETHYL-2-OXO-1,3-DIHYDRO-INDOLE Usage And Synthesis

Uses

6-Amino-3,3-dimethylindolin-2-one is a versatile reactant used in the preparation of selective and potent aminoisoquinoline derivatives as inhibitors of mutant B-Raf pathway. It is also used in the synthesis of pentacyclic aurora kinase inhibitors.

Synthesis

a) 3,3-Dimethyl-6-nitroindol-2-one (500 mg, 2.42 mmol) was dissolved in ethyl acetate (100 mL) and 10% palladium/activated carbon catalyst (129 mg, 121 μmol) was added. The reaction was stirred at 70 °C for 48 h under hydrogen atmosphere (balloon). After completion of the reaction, the catalyst was removed by filtration and the filtrate was washed with ethyl acetate. The filtrate was concentrated to give the orange powdery product 6-amino-3,3-dimethylindol-2-one (427 mg). The product was characterized by 1H NMR (DMSO-D6, 400 MHz): δ 10.75 (s, 1H), 7.92-7.89 (m, 1H), 7.62-7.58 (m, 2H), 1.30 (s, 6H).

References

[1] Patent: US2006/258689, 2006, A1. Location in patent: Page/Page column 35
[2] Patent: US4666923, 1987, A
[3] Patent: US2005/277643, 2005, A1
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 15, p. 4465 - 4475
[5] Patent: WO2014/40969, 2014, A1. Location in patent: Page/Page column 17

6-AMINO-3,3-DIMETHYL-2-OXO-1,3-DIHYDRO-INDOLE(100510-65-4)Related Product Information

• 6-AMINO-3,3-DIMETHYL-2,3-DIHYDRO-INDOLE
• 6-AMINO-3,3-DIMETHYL-2-OXO-1,3-DIHYDRO-INDOLE
• 2H-INDOL-2-ONE, 6-AMINO-1,3-DIHYDRO-