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Water → (5R)-5-{(E)-2-(5-chloro-6-methoxypyridin-2-yl)-2-[4-(propan-2-yl)phenyl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

HRID 70637
ノート
印刷プレビュー

反応式

HRID 70637 の反応式
Br[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([Cl:10])=[CH:4][CH:3]=1.[F-].[Cs+].[CH3:13][O:14][C:15]1[CH:51]=[C:50]([O:52][CH3:53])[CH:49]=[CH:48][C:16]=1[CH2:17][N:18]1[C@@H:22](/[CH:23]=[C:24](\[C:38]2[CH:43]=[CH:42][C:41]([CH:44]([CH3:46])[CH3:45])=[CH:40][CH:39]=2)/[Sn](CCCC)(CCCC)CCCC)[CH2:21][CH2:20][C:19]1=[O:47].O>CN(C)C=O.[Cu](I)I.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.C(OCC)(=O)C>[Cl:10][C:5]1[CH:4]=[CH:3][C:2](/[C:24](/[C:38]2[CH:39]=[CH:40][C:41]([CH:44]([CH3:46])[CH3:45])=[CH:42][CH:43]=2)=[CH:23]/[C@@H:22]2[N:18]([CH2:17][C:16]3[CH:48]=[CH:49][C:50]([O:52][CH3:53])=[CH:51][C:15]=3[O:14][CH3:13])[C:19](=[O:47])[CH2:20][CH2:21]2)=[N:7][C:6]=1[O:8][CH3:9]
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

9

反応物 4

HCID 962WaterHCID 25953Cesium fluorideHCID 58452258(5R)-1-(2,4-dimethoxybenzyl)-5-[(E)-2-[4-(propan-2-yl)phenyl]-2-(tributylstannyl)ethenyl]pyrrolidin-2-oneHCID 584523026-Bromo-3-chloro-2-methoxypyridine

生成物 1

HCID 67397494(5R)-5-{(E)-2-(5-chloro-6-methoxypyridin-2-yl)-2-[4-(propan-2-yl)phenyl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

6-bromo-3-chloro-2-methoxypyridine (361 mg), cesium fluoride (246 mg), copper iodide (170 mg) and tetrakis(triphenylphosphine)palladium(0) (92 mg) were added to a solution of (5R)-1-(2,4-dimethoxybenzyl)-5-[(E)-2-[4-(propan-2-yl)phenyl]-2-(tributylstannyl)ethenyl]pyrrolidin-2-one obtained in Reference Example 4-27 (543 mg) in N,N-dimethylformamide (6 mL), and the mixture was stirred at 65° C. for 1.5 hours. Water and ethyl acetate were added to the reaction solution. After filtration through celite, the organic layer was washed with brine. The organic layer dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→0:1) to give (5R)-5-{(E)-2-(5-chloro-6-methoxypyridin-2-yl)-2-[4-(propan-2-yl)phenyl]ethenyl}-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one as a yellow oil (268 mg).

後処理

  1. filtrationAfter filtration through celite
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic layer dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customafter which the solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→0:1)

出典と根拠

ORDレコード
ord-5d0cd933178c4fa0b238c6c3fefe6439
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822503B2

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