Electric Literature of 71294-03-6,Some common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-one, molecular formula is C8H6FNO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Step 1a: Preparation of 7-fluoro-1-methyl-1,3-dihydro-indol-2-one (7) This is similar to the procedure described in G. W. Rewcastle, B. D. Palmer, E. M. Dobrusin, D. W. Fry, A. J. Kracker and W. A. Deny, Journal of Medicinal Chemistry, 1994, 37, 2033-2042. A suspension of the 7-fluoro-1,3-dihydro-indol-2-one (9, 1.0 g, 6.62 mmol.) in H2O (30 mL) and NaOH (0.397 g, 9.92 mmol., 1.50 eq.) was treated with dimethyl sulfate (1.24 g, 9.86 mmol., 1.49 eq., 0.933 mL; added all at once) and heated to 100 C. for approx. 10 min. and then allowed to cooled to about 50 C. An additional 1.0 eq. of NaOH (0.265 g) and then additional 1 eq. of dimethyl sulfate (0.835 g, 0.626 mL) were added. Again heated to 100 for approx. 10 min. Then cooled to 0 C. in an ice bath and stirred and then filtered off solids, washed several times with water and dried on buchner funnel under vacuum overnight to yield the title compound as a solid. 1H NMR (400 MHz, CHLOROFORM-D) delta ppm 3.4 (d, J=2.5 Hz, 3H) 3.5 (s, 2H) 6.9 (m, 3H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoroindolin-2-one, its application will become more common.
Reference:
Patent; Josyula, Vara Prasad Venkata Nagendra; Gordeev, Mikhail; Luehr, Gary; US2006/229349; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem