반응 #1014735

반응 방정식

Cyclopropanamine

bis(diphenylphosphino)-1,1′-binaphthalene

cesium carbonate

5-bromo-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid methyl ester

→

title compound

수율 82.0%

5-(Cyclopropylamino)-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid methyl ester

수율 82.0%

용매

toluene

반응 조건

후처리

1. 1
   농축concentrated in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in water
3. 3
   추출extracted with ethyl acetate (30 mL)
4. 4
   workup.ADDITIONThe pH of the aqueous layer was adjusted to 2 by addition of 1 N HCl
5. 5
   여과the resulting precipitate was collected by filtration
6. 6
   기타dried in vacuo
7. 7
   기타purified by column chromatography (silica gel, 50 g, 50% ethyl acetate in petroleum ether)

실험 절차

Cyclopropanamine (CAS 765-30-0, 158 mg, 2.8 mmol), bis(diphenylphosphino)-1,1′-binaphthalene (CAS 98327-87-8, 115 mg, 0.19 mmol), tris(dibenzylideneacetone)dipalladium (CAS 51364-51-3, 84 mg, 0.093 mmol) and cesium carbonate (CAS 534-17-8, 1.8 g, 6.6 mmol) were added to solution of 5-bromo-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid methyl ester (Example 114 a, 530 mg, 1.85 mmol) in toluene (20 mL) under a nitrogen atmosphere. The reaction mixture was stirred overnight at 110° C. and concentrated in vacuo. The residue was dissolved in water and extracted with ethyl acetate (30 mL). The pH of the aqueous layer was adjusted to 2 by addition of 1 N HCl, the resulting precipitate was collected by filtration, dried in vacuo and purified by column chromatography (silica gel, 50 g, 50% ethyl acetate in petroleum ether) to yield the title compound (400 mg, 82%) as a yellow solid; MS (EI): m/e=263.1 [M+H]+.

출처