Reaktion #217534

Reaktionsgleichung

[(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

Ausbeute 199.9%

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

Ausbeute 199.9%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis cooled to 20° C.
2. 2
   workup.STIRRINGThe resulting mixture was stirred at room temperature for 1.5 hours
3. 3
   Einengenafter 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
   Einengenafter which it was concentrated in vacuo
7. 7
   Sonstigepartitioned between ethyl acetate and acidic Na2S2O4
8. 8
   TrocknenThe organic layer was dried over MgSO4
9. 9
   Einengenconcentrated in vacuo

Vorschrift

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−]

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