8-Hydroxyquinoline → Benzyl 4-(1-(4-(methylthio)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

HRID 1518459

반응식

HRID 1518459 반응식
[O:1]=[C:2]1[CH:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:4][NH:3]1.Br[C:26]1[CH:31]=[CH:30][C:29]([S:32][CH3:33])=[CH:28][CH:27]=1.N1C2C(=CC=CC=2O)C=CC=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O.[Cu]I>[CH3:33][S:32][C:29]1[CH:30]=[CH:31][C:26]([N:3]2[CH:4]=[CH:5][C:6]([O:8][CH:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[O:16])[CH2:11][CH2:10]3)=[CH:7][C:2]2=[O:1])=[CH:27][CH:28]=1

참가 물질

8

반응물 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 660374-BromothioanisoleHCID 67366192Benzyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate

생성물 1

HCID 67368480Benzyl 4-(1-(4-(methylthio)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate수율 95.4%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
145 °C

실험 절차

A mixture of benzyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate (697 mg, 2.12 mmol), (4-bromophenyl)(methyl)sulfane (431 mg, 2.12 mmol, Aldrich), quinolin-8-ol (61.6 mg, 0.425 mmol, Alfa Aesar), potassium carbonate (381 mg, 2.76 mmol, EMD), Copper(I) iodide (81 mg, 0.43 mmol, Alfa Aesar) in DMSO (6 mL) was stirred at 145° C. overnight under Argon. The resulting mixture was diluted with H2O and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to a green solid. The solid was purified by flash chromatography (SiO2, 0 to 5% MeOH in CH2Cl2) to yield 911 mg of desired product as a light green solid. MS (ESI) 451 (M+H).

후처리

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo to a green solid
  5. customThe solid was purified by flash chromatography (SiO2, 0 to 5% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-653794255f624c9dadb99358ca5345eb
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232404B2

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