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Cesium fluoride → Tert-butyl 4-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperazine-1-carboxylate

HRID 2172858
ノート
印刷プレビュー

反応式

HRID 2172858 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][N:9]=2)[C:5]([Cl:16])=[CH:4][N:3]=1.[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[F-].[Cs+]>CS(C)=O.CCOC(C)=O>[Cl:16][C:5]1[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][N:9]=2)=[CH:7][C:2]([N:20]2[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21]2)=[N:3][CH:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 25953Cesium fluorideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 866919052',5'-Dichloro-3,5-dimethyl-2,4'-bipyridine

生成物 1

HCID 67508218Tert-butyl 4-(5'-chloro-3,5-dimethyl-2,4'-bipyridin-2'-yl)piperazine-1-carboxylate収率 78.1%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
120 °C

実験手順

To a solution of 2′,5′-dichloro-3,5-dimethyl-2,4′-bipyridine (4.5 g, 17.8 mmol) and tert-butyl piperazine-1-carboxylate (4.0 g, 21.4 mmol) in DMSO (80 mL) was added CsF (5.4 g, 35.6 mmol). Then the mixture was heated at 120° C. for 18 hours. TLC (petroleum ether/EtOAc=2:1) showed that the reaction was complete. It was diluted with EtOAc (200 mL), washed with H2O (70 mL) and brine (70 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (petroleum ether/EtOAc=3:1) to afford title compound (5.6 g, 78%) as white solid.

後処理

  1. washwashed with H2O (70 mL) and brine (70 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (petroleum ether/EtOAc=3:1)

出典と根拠

ORDレコード
ord-bd458a8c2dca4990b9939359ea3404ee
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09056865B2

反応ノート

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