Sodium Iodide → (R)-4-((R)-1-(7-iodoquinolin-5-yloxy)ethyl)pyrrolidin-2-one

HRID 1496870ノート

反応式

HRID 1496870 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([O:12][C@@H:13]([C@H:15]2[CH2:19][NH:18][C:17](=[O:20])[CH2:16]2)[CH3:14])[CH:3]=1.CNCCNC.[I-:27].[Na+]>O1CCOCC1.C(Cl)Cl.[Cu]I>[I:27][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[C:4]([O:12][C@@H:13]([C@H:15]2[CH2:19][NH:18][C:17](=[O:20])[CH2:16]2)[CH3:14])[CH:3]=1

参加物

7

反応物 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 71238288(R)-4-((R)-1-(7-bromoquinolin-5-yloxy)ethyl)pyrrolidin-2-one

生成物 1

HCID 71238317(R)-4-((R)-1-(7-iodoquinolin-5-yloxy)ethyl)pyrrolidin-2-one収率 26.3%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

50 mg of Example 27 and 9 mg of copper (I) iodide were suspended in 300 μL dioxane under argon. 9.6 μL N,N′dimethylethylendiamine and 45 mg of sodium iodide were added and the mixture heated to 110° C. over weekend. The mixture was diluted with DCM and extracted with aqueous ammonia and water, the organic phase was subsequently concentrated in vacuo and the residual purified with HPLC (XbridgeC18; MeOH/water, TFA) to yield 15 mg yellow solid as Example 37.

後処理

  1. extractionextracted with aqueous ammonia and water
  2. concentrationthe organic phase was subsequently concentrated in vacuo
  3. customthe residual purified with HPLC (XbridgeC18; MeOH/water, TFA)

出典と根拠

ORDレコード
ord-404176f67322467a8d9e4d43fa960add
出典データセット
uspto-grants-2015_12
特許番号
US09199937B2

反応ノート

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