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Cesium carbonate → [4-({3-[3-Methyl-8-(Trifluoromethyl)Quinolin-4-yl]Phenoxy}Methyl)Phenyl]Acetic Acid

HRID 2104602
ノート
印刷プレビュー

反応式

HRID 2104602 の反応式
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:19]([F:22])([F:21])[F:20].Br[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][CH2:24][C:25]1[CH:26]=[CH:27][C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:29][CH:30]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:19]([F:22])([F:20])[F:21]
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

5

反応物 3

HCID 10796Cesium carbonateHCID 45190564-(Bromomethyl)phenylacetic acidHCID 665862653-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenol

生成物 1

HCID 16718749[4-({3-[3-Methyl-8-(Trifluoromethyl)Quinolin-4-yl]Phenoxy}Methyl)Phenyl]Acetic Acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

3-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenol (1.13 g, 3.73 mmol) and 4-bromomethylphenylacetic acid (1.02 g, 4.47 mmol) in CH2Cl2 (60 mL) is treated with Cs2CO3 (4.86 g, 14.9 mmol) and the reaction is stirred overnight. The solvent is removed and the residue dissolved in THF and 2N aq NaOH. After heating at 70° C. for 1 h, the reaction is cooled and the layers separated. The aqueous layer is further extracted with ethyl acetate. The combined organics are dried (Na2SO4) and concentrated. The residue is chromatographed eluting with 20:80 ethyl acetate:hexane and then 5:95 methanol:methylene chloride to afford the title product.

後処理

  1. customThe solvent is removed
  2. dissolutionthe residue dissolved in THF
  3. temperaturethe reaction is cooled
  4. customthe layers separated
  5. extractionThe aqueous layer is further extracted with ethyl acetate
  6. dry with materialThe combined organics are dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue is chromatographed
  9. washeluting with 20:80 ethyl acetate

出典と根拠

ORDレコード
ord-b5d2507d4be84c6eb619f3d095950bc2
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07576215B2

反応ノート

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