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Cesium carbonate → (E)-4-methyl-2-(prop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester

HRID 2093721
ノート
印刷プレビュー

反応式

HRID 2093721 の反応式
C([O-])([O-])=O.[Cs+].[Cs+].[CH2:7]([O:9][C:10]([C:12]1[C:13](OS(C(F)(F)F)(=O)=O)=[N:14][C:15]2[C:20]([C:21]=1[CH3:22])=[CH:19][CH:18]=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)=[O:11])[CH3:8].[CH:35](/B(O)O)=[CH:36]\[CH3:37].C(O)C.C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(=O)OCC.CCCCCC>[CH2:7]([O:9][C:10]([C:12]1[C:13](/[CH:35]=[CH:36]/[CH3:37])=[N:14][C:15]2[C:20]([C:21]=1[CH3:22])=[CH:19][CH:18]=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)=[O:11])[CH3:8]
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

7

反応物 4

HCID 10796Cesium carbonateHCID 6157276((1E)-prop-1-en-1-yl)boronic acidHCID 21863594Toluene ethanolHCID 866626824-Methyl-7-(trifluoromethyl)-2-(trifluoromethylsulfonyl-oxy)quinoline-3-carboxylic acid ethyl ester

生成物 1

HCID 66583793(E)-4-methyl-2-(prop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester収率 75%

試薬・触媒・溶媒

2
HCID 178418397HCID 178418397、化合物触媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
110 °C

実験手順

1.8 g (5.6 mmol) Cs2CO3 and 210 mg (0.2 mmol) Pd(PPh3)4 were added to a solution of 800 mg (1.9 mmol) 4-methyl-7-(trifluoromethyl)-2-(trifluoromethyl-sulfonyloxy)-quinoline-3-carboxylic acid ethyl ester and 320 mg (3.7 mmol) (E)-propene-1-yl-boronic acid in an ethanol/toluene mixture (1:9 vv, 20 ml) and the mixture was heated to 110° C. for 1 h. The mixture was thereafter concentrated in a vacuum and the residue was taken up with EtOAc (20 ml) and water (20 ml). The organic phase was separated, washed with water and brine, dried over Na2SO4 and concentrated in a vacuum. After CC (EA/hexane 1:9) of the residue, 450 mg (1.4 mmol, 75%) (E)-4-methyl-2-(prop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester was obtained.

後処理

  1. concentrationThe mixture was thereafter concentrated in a vacuum
  2. customThe organic phase was separated
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in a vacuum

出典と根拠

ORDレコード
ord-ee15b7fba11342268d805fee9a0e843e
出典データセット
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08445512B2

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