反応 #2336529

反応方程式

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

N-(2-(4-CHLOROPHENYL)ETHYL)-3-HYDROXYPYRIDINE-2-CARBOXAMIDE

溶媒

CH2Cl2

CH2Cl2

EtOAc

反応条件

後処理

1. 1
   その他The organic layer was separated
2. 2
   抽出the aqueous layer extracted with CH2Cl2 (2×10 mL)
3. 3
   乾燥dried (MgSO4)
4. 4
   濃縮concentrated
5. 5
   その他to give a gummy solid
6. 6
   その他for 30 minutes
7. 7
   ろ過The mixture was filtered
8. 8
   洗浄washed with 0.1N HCl (20 mL)
9. 9
   乾燥dried (MgSO4)
10. 10
    濃縮concentrated

実験手順

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. COUPLING PROCEDURE C: PREPARATION OF N-(4-CYCLOHEXYLPHENYL)-3-HYDROXYPYRIDINE-2-CARBOXAMIDE.

出典