8-Hydroxyquinoline → (S)-tert-butyl 2-(4-(3-(4-fluorophenyl)-1H-1,2,4-triazol-1-yl)phenyl)morpholine-4-carboxylate

HRID 710259노트

반응식

HRID 710259 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[CH:11][NH:10][N:9]=2)=[CH:4][CH:3]=1.Br[C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]2[O:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].OC1C=CC=C2C=1N=CC=C2>CN(C)C=O.O.[Cu]I.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[CH:11][N:10]([C:14]3[CH:15]=[CH:16][C:17]([C@@H:20]4[O:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]4)=[CH:18][CH:19]=3)[N:9]=2)=[CH:6][CH:7]=1

참가 물질

9

반응물 4

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 58097875tert-butyl (2S)-2-(4-bromophenyl)morpholine-4-carboxylateHCID 178505560HCID 178505560, 화합물

생성물 1

HCID 89689407(S)-tert-butyl 2-(4-(3-(4-fluorophenyl)-1H-1,2,4-triazol-1-yl)phenyl)morpholine-4-carboxylate

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
150 °C

실험 절차

3-(4-Fluorophenyl)-1H-1,2,4-triazole (CAS [95728-10-2], 200 mg, 0.9 mmol) was dissolved in a mixture of dimethylformamide and water (5.5 ml; v/v=10:1) and (S)-tert-butyl 2-(4-bromophenyl)morpholine-4-carboxylate (368 mg, 1.08 mmol), cesium carbonate (1.46 g, 4.48 mmol), copper(I)-iodide (5.1 mg, 0.027 mmol) and 8-hydroxyquinoline (4 mg, 0.027 mmol) were added successively. The glass was closed and the reaction mixture was allowed to stir at 150° C. for 48 h. According to TLC, the reaction was finished. After cooling, water and ethyl acetate were added. The organic layer was dried over MgSO4 and evaporated. The crude material was purified by flash chromatography (silica gel, gradient heptane/ethyl acetate), off-white solid (205 mg, 54%), MS (ISP): 425.2 ([M+H]+).

후처리

  1. additionwere added successively
  2. customThe glass was closed
  3. temperatureAfter cooling
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated
  6. customThe crude material was purified by flash chromatography (silica gel, gradient heptane/ethyl acetate), off-white solid (205 mg, 54%), MS (ISP)

출처 및 근거

ORD 기록
ord-e44baf33de2b491795532accbeb81cd4
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181230B2

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