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N,N'-Dimethylethylenediamine → tert-butyl 4-[1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxopiperazine-1-carboxylate

HRID 1622883
ノート
印刷プレビュー

反応式

HRID 1622883 の反応式
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:8][CH:9]=2)[N:4]([CH3:19])[CH:3]=1.[O:20]=[C:21]1[NH:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>[Cu]I.O.O1CCOCC1>[CH3:19][N:4]1[C:5]2=[N:6][C:7]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[CH:8][CH:9]=[C:10]2[C:2]([N:26]2[CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH2:22][C:21]2=[O:20])=[CH:3]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 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 678161163-Bromo-1-methyl-6-(2-pyridylmethoxy)pyrrolo[2,3-b]pyridine

生成物 1

HCID 67817033tert-butyl 4-[1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-3-oxopiperazine-1-carboxylate収率 88.6%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 3-bromo-1-methyl-6-(pyridin-2-ylmethoxy)-1H-pyrrolo[2,3-b]pyridine (0.226 g, 0.71 mmol), tert-butyl 3-oxopiperazine-1-carboxylate (0.20 g, 1 mmol), copper (I) iodide (0.027 g, 0.142 mmol) and potassium phosphate (0.212 g, 1 mmol) is purged under a nitrogen atmosphere in a reaction tube. 1,4-Dioxane (3 mL) and N,N′-dimethylethylene diamine (0.031 mL, 0.288 mmol) are added, the tube sealed and the reaction mixture heated at 100° C. for 25 h. The reaction is cooled to room temperature, poured into water and extracted with EtOAc. The organic phase is dried over sodium sulphate, filtered and concentrated in vacuo. The residue is purified by column chromatography on silica eluting with hexane/EtOAc (1:1), followed by neat EtOAc, to give the title compound (0.275 g, 0.629 mmol) as a pale yellow solid. MS (m/z): 438 (M+1).

後処理

  1. customis purged under a nitrogen atmosphere in a reaction tube
  2. customthe tube sealed
  3. temperatureThe reaction is cooled to room temperature
  4. extractionextracted with EtOAc
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography on silica eluting with hexane/EtOAc (1:1)

出典と根拠

ORDレコード
ord-47d3311da1d04c9a894a4162a7096a65
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08778946B2

反応ノート

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