Potassium Iodide → 4-[3-(4-Cyclopropyl-piperazin-1-yl)-propoxy]-3-fluoro-benzoic Acid Ethyl Ester

HRID 220869노트

반응식

HRID 220869 반응식
Cl.Cl.[CH:3]1([N:6]2[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:20]([O:22][C:23](=[O:36])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33]Br)=[C:26]([F:35])[CH:25]=1)[CH3:21]>CC(C)=O>[NH3:6].[CH2:20]([O:22][C:23](=[O:36])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32][CH2:33][N:9]2[CH2:10][CH2:11][N:6]([CH:3]3[CH2:5][CH2:4]3)[CH2:7][CH2:8]2)=[C:26]([F:35])[CH:25]=1)[CH3:21]

참가 물질

7

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 212208121-Cyclopropylpiperazine dihydrochlorideHCID 575553074-(3-Bromo-propoxy)-3-fluorobenzoic acid ethyl ester

생성물 2

HCID 222AmmoniaHCID 575554304-[3-(4-Cyclopropyl-piperazin-1-yl)-propoxy]-3-fluoro-benzoic Acid Ethyl Ester수율 89%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

1-Cyclopropyl-piperazine dihydrochloride (642 mg, 3.2 mmol, according to the procedure described by G. S. Poindexter, M. A. Bruce, K. L. Le Boulluec, I. Monkovic, Tet. Lett., 35(44), 7331-7334, 1994), potassium carbon-ate (2.1 g, 15.2 mmol) and potassium iodide (50 mg, 0.3 mmol) were added to 4-(3-bromo-propoxy)-3-fluoro-benzoic acid ethyl ester from Example E48.1 (1.2 g, 3.9 mmol) in acetone (25 ml). The mixture was heated at reflux for 20 h. The solid was filtered off, washed with EtOAc and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; EtOAc then 1% 35% ammonia:9% methanol:90% dichloromethane) to yield the title compound (1.0 g, 89%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 h
  3. filtrationThe solid was filtered off
  4. washwashed with EtOAc
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (eluant

출처 및 근거

ORD 기록
ord-c98fd37e81ea4f8f8f44c42142e3838d
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

반응 노트

불러오는 중…