6-bromo-7-fluoroisatin Chemical Properties

Density 

1.907±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

7.42±0.20(Predicted)

Appearance

Yellow to brown Solid

InChI

InChI=1S/C8H3BrFNO2/c9-4-2-1-3-6(5(4)10)11-8(13)7(3)12/h1-2H,(H,11,12,13)

InChIKey

GVZVXBNHVMAAAK-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC(Br)=C2F)C(=O)C1=O

6-bromo-7-fluoroisatin Usage And Synthesis

Uses

6-?Bromo-?7-?fluoroindoline-?2,?3-?dione is a heterocyclic reagent used in the synthesis of electrophiles capable of targeting K-Ras oncogense in the treatment of cancer.

Synthesis

N-(3-bromo-2-fluorophenyl)-2-(hydroxyimino)acetamide (1.82 g, 7.03 mmol) was used as a raw material, which was slowly added to concentrated sulfuric acid (20 mL) at 60°C. Subsequently, the temperature of the reaction system was raised to 90°C and the reaction was maintained at this temperature for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and carefully poured into ice water. The precipitated yellow precipitate was collected by filtration and dried to give 6-bromo-7-fluorodihydroindole-2,3-dione (1.41 g, 82% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 11.75 (s, 1H), 7.39 (dd, J = 5.7,7.9 Hz, 1H), 7.31 (d, J = 8.2 Hz, 1H).

References

[1] Patent: WO2015/54572, 2015, A1. Location in patent: Page/Page column 253
[2] Patent: WO2017/87528, 2017, A1. Location in patent: Page/Page column 180; 181
[3] Patent: WO2017/58915, 2017, A1. Location in patent: Page/Page column 102
[4] Patent: US2018/15087, 2018, A1. Location in patent: Paragraph 0320
[5] Patent: WO2011/119704, 2011, A1. Location in patent: Page/Page column 40