Cesium carbonate → N-(3,4-Difluorobenzyl)-2-isopropyl-1-(pyridin-2-ylmethyl)-6-(pyridin-2-yloxy)-1H-indole-3-carboxamide

HRID 40167

反応式

HRID 40167 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([OH:18])=[CH:15][CH:16]=2)[N:11]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[C:10]=1[CH:26]([CH3:28])[CH3:27])=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].I[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=1>CN(C)C=O.[Cu]>[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=3)=[CH:15][CH:16]=2)[N:11]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[C:10]=1[CH:26]([CH3:28])[CH3:27])=[O:8]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2211262-IodopyridineHCID 59762365N-(3,4-Difluorobenzyl)-6-hydroxy-2-isopropyl-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide2 回

生成物 1

HCID 59762396N-(3,4-Difluorobenzyl)-2-isopropyl-1-(pyridin-2-ylmethyl)-6-(pyridin-2-yloxy)-1H-indole-3-carboxamide

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of N-(3,4-difluorobenzyl)-2-isopropyl-6-hydroxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide (Compound 220, 26 mg, 0.060 mmol) in dimethylformamide (1 ml) stirring at room temperature, was added cesium carbonate (83 mg, 0.25 mmol) and the reaction stirred for 5 minutes. 2-iodopyridine (0.05 mL, 0.09 g, 0.47 mmol) and then copper powder (7.0 mg, 0.11 mmol) was then directly added and the resulting mixture heated at 100° C. for 18 h. The reaction was cooled to room temperature, quenched with water, extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (50% EtOAc-hexanes, 100 % EtOAc) to yield the title compound as a white solid.

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel (50% EtOAc-hexanes, 100 % EtOAc)

出典と根拠

ORDレコード
ord-fe7ab3385e7e4a2188222dc5a2b9fb58
出典データセット
uspto-grants-2013_09
特許番号
US08524917B2

関連ノート

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