반응 #1146864

반응 방정식

4-(4-trifluoromethylphenoxy) aniline

3-benzyloxy-6-bromo-4-methoxypyridin-2-carbonylchloride

6-bromo-3-benzyloxy-4-methoxypyridine-2-carbonyl Chloride

triethylamine

hydrogen

HCl

→

title compound

수율 43.3%

3-Hydroxy-4-Methoxy-N-(4-(4-Trifluoromethylphenoxy)Phenyl)-Pyridine-2-Carboxamide

수율 43.3%

용매

CH2Cl2

CH2Cl2

EtOAc

반응 조건

후처리

1. 1
   기타The organic layer was separated
2. 2
   추출the aqueous layer extracted with CH2Cl2 (2×10 mL)
3. 3
   건조dried (MgSO4)
4. 4
   농축concentrated
5. 5
   기타to give a gummy solid
6. 6
   기타for 30 minutes
7. 7
   여과The mixture was filtered
8. 8
   세척washed with 0.1N HCl (20 mL)
9. 9
   건조dried (MgSO4)
10. 10
    농축concentrated

실험 절차

To a stirred solution of 4-(4-trifluoromethylphenoxy) aniline (0.20 g, 0.8 mmol) and DMAP (0.10 g, 0.085 mmol) in CH2Cl2 (10 mL) was added all at once a solution of 3-benzyloxy-6-bromo-4-methoxypyridin-2-carbonylchloride (3) (0.29 g, 0.8 mmol) in CH2Cl2 (5 mL). The resulting mixture was stirred overnight at room temperature then poured into 2N HCl (10 mL). The organic layer was separated and the aqueous layer extracted with CH2Cl2 (2×10 mL). The organic layers were combined, dried (MgSO4) and concentrated to give a gummy solid. This solid was taken up in EtOAc (20 mL), and triethylamine (0.80 g, 0.8 mmol) and 5% Pd on carbon (0.10 g) were added. The resulting mixture was subjected to a hydrogen atmosphere (initial pressure=50 psi) on a Parr shaker for 30 minutes. The mixture was filtered, washed with 0.1N HCl (20 mL), dried (MgSO4) and concentrated to give the title compound as an off-white solid (0.14 g), m.p.=122-129° C.

출처