Cesium carbonate → HCID 68325766、化合物

HRID 2403294ノート

反応式

HRID 2403294 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.Cl[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([NH:1][C:2]2[N:7]=[CH:6][C:5]([CH:8]3[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]3)=[CH:4][CH:3]=2)=[N:23][CH:24]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 276852,5-DichloropyridineHCID 68325614HCID 68325614、化合物

生成物 1

HCID 68325766HCID 68325766、化合物収率 29%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

tert-Butyl (RS)-2-(6-aminopyridin-3-yl)morpholine-4-carboxylate (55 mg), 2,5-dichloropyridine (29 mg, CAS 16110-09-1) and cesium carbonate (96 mg) were combined with dioxane (2 ml) to give a yellow suspension. The mixture was degassed by bubbling argon into the mixture for several minutes. Xantphos (6.84 mg) and tris(dibenzylideneacetone)dipalladium chloroform complex (6.11 mg) were then added. The reaction mixture was then capped and stirred at 100° C. overnight. The crude reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography (silica gel; gradient: 0% to 80% EtOAc in hexanes) to afford tert-butyl 2-(6-(5-chloropyridin-2-ylamino)pyridin-3-yl)morpholine-4-carboxylate (22 mg, 29%) as a yellow solid. MS (ISP): 393.2 ([{37Cl}M+H]+), 391.2 ([{35Cl}M+H]+).

後処理

  1. customto give a yellow suspension
  2. customThe mixture was degassed
  3. customby bubbling argon into the mixture for several minutes
  4. additionXantphos (6.84 mg) and tris(dibenzylideneacetone)dipalladium chloroform complex (6.11 mg) were then added
  5. customThe reaction mixture was then capped
  6. customThe crude reaction mixture
  7. temperaturewas cooled to room temperature
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. customthe residue was purified by flash column chromatography (silica gel; gradient: 0% to 80% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-5c34385bf0b84b9887d1e23e398aebb3
出典データセット
uspto-grants-2014_08
特許番号
US08802673B2

反応ノート

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