Reacción #302851

Ecuación de reacción

compound 8

6-(tributylstannyl)-4′-methylaminoflavone

iodine

sodium bisulfite

→

compound 10

6-iodo-4′-methylaminoflavone

Disolventes

chloroform

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat room temperature
2. 2
   OtroThe obtained mixture was reacted at room temperature for 10 minutes
3. 3
   Otroso as to terminate
4. 4
   Otrothe reaction
5. 5
   OtroThe chloroform layer was separated
6. 6
   Secadoit was then dried over sodium sulfate
7. 7
   workup.DISTILLATIONThereafter, the solvent was distilled away under reduced pressure

Procedimiento

A chloroform solution of iodine (1.5 ml, 1 M) was added to a chloroform solution (20 ml) that contained compound 8 (100 mg, 0.185 mmol) at room temperature. The obtained mixture was reacted at room temperature for 10 minutes, and a saturated sodium bisulfite aqueous solution (15 ml) was then added thereto, so as to terminate the reaction. The chloroform layer was separated, and it was then dried over sodium sulfate. Thereafter, the solvent was distilled away under reduced pressure, and the residue was then subjected to silica gel column chromatography using ethyl acetate/hexane (1/2) as an elution solvent, so as to obtain a product of interest, 6-iodo-4′-methylaminoflavone (compound 10). Yield: 20 mg (yield constant: 28.7%) 1H NMR (300 MHz, CDCl3) δ8.53 (s, 1H), 7.90 (d, J=9.0 Hz, 1H), 7.75 (d, J=8.4 Hz, 2H), 7.28 (d, J=10.8 Hz, 1H), 6.64-6.69 (m, 3H), 4.15 (s, 1H), 2.93 (s, 3H). MS m/z 377 (M+).

Fuente