반응 #2201605

반응 방정식

CH2Cl2

{4-[(ethyloxy)carbonyl]phenyl}boronic acid

[(1R)-1-(4-Bromophenyl)-2-(4-morpholinyl)ethyl]methylamine

K2CO3

→

title compound

수율 107.5%

Ethyl 4′-[(1R)-1-(methylamino)-2-(4-morpholinyl)ethyl]-4-biphenylcarboxylate

수율 107.5%

용매

EtOH

반응 조건

후처리

1. 1
   여과filtered through celite
2. 2
   농축The filtrate was concentrated
3. 3
   기타partitioned between EtOAc and brine
4. 4
   건조The organic layer was dried over MgSO4
5. 5
   여과filtered
6. 6
   농축The filtrate was concentrated

실험 절차

[(1R)-1-(4-Bromophenyl)-2-(4-morpholinyl)ethyl]methylamine (20.0 g, 66.9 mmol) was dissolved in EtOH (500 mL) at room temperature with magnetic stirring. The resulting solution was treated with {4-[(ethyloxy)carbonyl]phenyl}boronic acid (14.5 g, 73.6 mmol) followed by K2CO3 (27.7 g, 200.7 mmol) and PdCl2(dppf)2.CH2Cl2 (2.73 g, 3.34 The reaction was maintained at 80° C. overnight. The reaction mixture was cooled to room temperature and then filtered through celite. The filtrate was concentrated and then partitioned between EtOAc and brine. The organic layer was dried over MgSO4, and filtered. The filtrate was concentrated to give the title compound as a brown oil (26.5 g, 80% purity). MS (ES) m/e 369 [M+H]−.

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