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Cesium carbonate → ethyl (2E)-3-(6-{[(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate

HRID 2376034
ノート
印刷プレビュー

反応式

HRID 2376034 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:21][C:22]1[CH:35]=[CH:34][C:25]([C:26]([N:28]2[CH2:32][CH2:31][C@@H:30]([NH2:33])[CH2:29]2)=[O:27])=[CH:24][CH:23]=1>O1CCOCC1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(N(C)C)=CC=CC=2)CCCCC1>[Cl:21][C:22]1[CH:35]=[CH:34][C:25]([C:26]([N:28]2[CH2:32][CH2:31][C@@H:30]([NH:33][C:2]3[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=3)[CH2:29]2)=[O:27])=[CH:24][CH:23]=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

8

反応物 3

HCID 10796Cesium carbonateHCID 108461873-(6-Chloro-pyridin-3-yl)-acrylic acid ethyl esterHCID 68963176(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinamine

生成物 1

HCID 86603659ethyl (2E)-3-(6-{[(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate収率 32.7%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate
触媒
HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl触媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a solution of ethyl (2E)-3-(6-chloro-3-pyridyl)acrylate (3.5 g) in dioxane (70 mL) was added palladium(II) acetate (371 mg) and 2′-(dicyclohexylphosphino)-N,N-dimethyl-2-biphenylamine (110 mg) and cesium carbonate (583 mg), and (3R)-1-(4-chlorobenzoyl)-3-pyrrolidinamine (4.09 g). The mixture was heated at 90° C. for 3 hours. The resulting mixture was diluted with AcOEt, and the precipitate was removed by filtration. The filtrate was concentrated and residual brown oil was purified by purified by silica gel column chromatography eluted with AcOEt and hexane (1:4)-AcOEt to give ethyl (2E)-3-(6-{[(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate (2.16 g) as dark yellow form.

後処理

  1. customthe precipitate was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. customresidual brown oil was purified
  4. customby purified by silica gel column chromatography
  5. washeluted with AcOEt and hexane (1:4)-AcOEt

出典と根拠

ORDレコード
ord-095b240c2a4d4283ac372fc039136bbf
出典データセット
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07465731B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート