| Identification | Back Directory | [Name]
6-AMINO-3,3-DIMETHYL-2-OXO-1,3-DIHYDRO-INDOLE | [CAS]
100510-65-4 | [Synonyms]
AP3Impurity6
6-Amino-3,3-dimethylindolin-2-one
6-amino-3,3-dimethyl-1H-indol-2-one
6-Amino-3,3-dimethyl-1H-indolin-2-one
6-Amino-3,3-dimethyl-1,3-dihydro-indol-2-one
6-AMINO-3,3-DIMETHYL-2-OXO-1,3-DIHYDRO-INDOLE
6-Amino-1,2-dihydro-3,3-dimethyl-2-oxo-3H-indole
2H-Indol-2-one, 6-amino-1,3-dihydro-3,3-dimethyl- | [Molecular Formula]
C10H12N2O | [MDL Number]
MFCD11053509 | [MOL File]
100510-65-4.mol | [Molecular Weight]
176.22 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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