Reaktion #731351

Reaktionsgleichung

N-(5-Chloropyridin-2-yl)-2-aminobenzamide

2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoic acid

pyridine

pyridine

oxalyl chloride

→

desired product

Ausbeute 85.0%

2-[4-Fluoro-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide

Ausbeute 85.0%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeVigorous bubbling
2. 2
   Einengenthe reaction was concentrated in vacuo
3. 3
   workup.ADDITIONThe residue was diluted with methylene chloride (20 mL)
4. 4
   Waschenwashed with water (2×10 mL)
5. 5
   TrocknenThe organic layer was dried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe crude residue was purified by flash column chromatography (100% CH2Cl2 to 10% EtOAc/CH2Cl2)

Vorschrift

The 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoic acid (507 mg, 2.05 mmol) was diluted with methylene chloride (20 mL). DMF (4 drops) and pyridine (0.2 mL, 2.47 mmol) were added, followed by oxalyl chloride (0.2 mL, 2.29 mmol). Vigorous bubbling occurred. After 1.5 hours, the reaction was concentrated in vacuo. The residue was diluted with methylene chloride (20 mL). N-(5-Chloropyridin-2-yl)-2-aminobenzamide (507 mg, 2.05 mmol) was added, followed by pyridine (0.2 mL, 2.47 mmol). After stirring overnight, the reaction was diluted with methylene chloride (100 mL) and washed with water (2×10 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated. The crude residue was purified by flash column chromatography (100% CH2Cl2 to 10% EtOAc/CH2Cl2) to give the desired product (992 mg, 1.74 mmol, 85%) as a white solid.

Quelle