Reacción #217534

Ecuación de reacción

[(2-bromo-4-{[(3,4-dichloro-phenyl)-(4-phenyl-thiazol-2-yl)-amino]-methyl}-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester

bistrimethylsilyltrifluoroacetamide

iodotrimethylsilane

→

white foam

Rendimiento 199.9%

[(2-Bromo-4-{[(3,4-dichloro-phenyl)-(4-phenyl-thiazol-2-yl)-amino]-methyl}-phenyl)-difluoro-methyl]-phosphonic acid

Rendimiento 199.9%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais cooled to 20° C.
2. 2
   workup.STIRRINGThe resulting mixture was stirred at room temperature for 1.5 hours
3. 3
   Concentraciónafter which it was concentrated in vacuo
4. 4
   workup.STIRRINGThe resulting material was stirred in CH3CN (4 mL)
5. 5
   workup.WAITH2O (0.5 mL), and TFA (0.5 mL) for 0.5 hours
6. 6
   Concentraciónafter which it was concentrated in vacuo
7. 7
   Otropartitioned between ethyl acetate and acidic Na2S2O4
8. 8
   SecadoThe organic layer was dried over MgSO4
9. 9
   Concentraciónconcentrated in vacuo

Procedimiento

To [(2-bromo-4-{[(3,4-dichloro-phenyl)-(4-phenyl-thiazol-2-yl)-amino]-methyl}-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester (0.176 g, 0.25 mmol) in CH2Cl2 (3 mL) was added bistrimethylsilyltrifluoroacetamide (0.66 g, 2.59 mmol) and reaction mixture was stirred at room temperature for 1 h after which the reaction mixture is cooled to 20° C. and iodotrimethylsilane (0.51 g, 2.59 mmol) is added drop wise. The resulting mixture was stirred at room temperature for 1.5 hours, after which it was concentrated in vacuo. The resulting material was stirred in CH3CN (4 mL), H2O (0.5 mL), and TFA (0.5 mL) for 0.5 hours, after which it was concentrated in vacuo and partitioned between ethyl acetate and acidic Na2S2O4. The organic layer was dried over MgSO4 and concentrated in vacuo to yield 0.31 g (99%) of a white foam; 1H NMR (300 MHz, DMSO-d6) δ 7.99-7.28 (m, 12 H), 5.33 (s, 2 H); LCMS m/z 619 [M−]

Fuente