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

HRID 710259ノート

反応式

HRID 710259 の反応式
[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

参加物

9

反応物 4

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 58097875tert-butyl (2S)-2-(4-bromophenyl)morpholine-4-carboxylateHCID 178505560HCID 178505560、化合物

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

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]+).

後処理

  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)

出典と根拠

ORDレコード
ord-e44baf33de2b491795532accbeb81cd4
出典データセット
uspto-grants-2015_11
特許番号
US09181230B2

反応ノート

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