Reacción #595384

Ecuación de reacción

compound 26A

4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-4-fluoro-1H-indazol-3-yl)-2-hydroxybenzoic acid

Ac2O

MgI2

→

title compound

2-acetoxy-4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-4-fluoro-1H-indazol-3-yl)benzoic acid

Disolventes

ethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was cooled to rt
2. 2
   Otroquenched with H2O
3. 3
   Extracciónextracted with ether
4. 4
   Concentraciónconcentrated
5. 5
   workup.DISSOLUTIONThe crude product was dissolved in THF (10 mL)/H2O (10 mL)
6. 6
   Temperaturarefluxed at 80° C. for 1 h
7. 7
   TemperaturaThe mixture was cooled to rt
8. 8
   workup.ADDITIONdiluted with H2O
9. 9
   Extracciónextracted with EtOAc
10. 10
    ConcentraciónThe combined organic extracts were concentrated
11. 11
    Otropurified by flash chromatography PE/EA (5/1)

Procedimiento

A suspension of compound 26A (48 mg, 0.1 mmol), Ac2O (0.8 mL) and MgI2 (28 mg, 0.1 mmol) in anhydrous ethyl ether (3 mL) was refluxed at 40° C. for 0.5 h. The reaction was cooled to rt, quenched with H2O, extracted with ether, and concentrated. The crude product was dissolved in THF (10 mL)/H2O (10 mL) and refluxed at 80° C. for 1 h. The mixture was cooled to rt, diluted with H2O, and extracted with EtOAc. The combined organic extracts were concentrated and purified by flash chromatography PE/EA (5/1) to give the title compound as a white solid. LCMS (ESI): calc'd for C22H12ClF4N2O4 [M+H]+: 521. found: 521, 1H NMR (400 MHz, MeOD) δ 8.47 (1H, d, J=8.0 Hz), 8.11 (1H, d, J=8.0 Hz), 7.90-7.76 (5H, m), 7.53 (1H, t, J=1.6 Hz), 3.34 (1H, q, J=8.0 Hz), 2.31 (3H, s).

Fuente