Reacción #57949

Ecuación de reacción

2-(3,5-bis-trifluoromethyl-benzoylamino)-4-(3-bromo-propoxy)-benzoic acid methyl ester

4-tert-butyl-benzaldehyde oxime

cesium carbonate

→

2-{[3,5-bis(trifluoromethyl)benzoyl]amino}-4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid methyl ester

Rendimiento 48.0%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was heated
2. 2
   Temperaturato reflux overnight
3. 3
   OtroThe mixture was partitioned between ethyl acetate and brine
4. 4
   Otrothe layers were then separated
5. 5
   ExtracciónThe aqueous layer was extracted with two additional portions of ethyl acetate
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroThe crude oil was purified by flash chromatography through silica gel

Procedimiento

To a solution of 2-(3,5-bis-trifluoromethyl-benzoylamino)-4-(3-bromo-propoxy)-benzoic acid methyl ester (0.53 g, 1.00 mmol) and 4-tert-butyl-benzaldehyde oxime (0.20 g, 1.10 mmol) in acetone (35 mL) was added cesium carbonate (1.30 g, 4.00 mmol). The mixture was heated to reflux overnight and then allowed to cool back to room temperature. The mixture was partitioned between ethyl acetate and brine and the layers were then separated. The aqueous layer was extracted with two additional portions of ethyl acetate. The organics were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude oil was purified by flash chromatography through silica gel using diethyl ether/hexanes (0/100 gradient to 5/95) to give 2-{[3,5-bis(trifluoromethyl)benzoyl]amino}-4-[3-({[(1E)-(4-tert-butylphenyl)methylidene]amino}oxy)propoxy]benzoic acid methyl ester (0.30 g, 48%) as an off-white solid. 1H NMR (400 MHz, CDCl3); δ 12.52 (s, 1H), 8.51 (d, 1H), 8.48 (s, 2H), 8.06 (s, 1H), 8.04 (s, 1H), 7.99 (d, 1H), 7.47-7.35 (AA′BB′, 4H), 6.67 (dd, 1H), 4.34 (t, 2H), 4.22 (t, 2H), 3.92 (s, 3H), 2.23 (m, 2H), 1.28 (s, 9H).

Fuente