Hydrochloric Acid → 1-Cyano-4-hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carboxylic acid ethyl ester

HRID 1480983ノート

反応式

HRID 1480983 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](I)[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH:10]=2)=[O:5])[CH3:2].[C:25]([Cu])#[N:26].Cl>CN1C(=O)CCC1.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:25]#[N:26])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([O:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[CH:10]=2)=[O:5])[CH3:2]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 898130004-Hydroxy-1-iodo-7-(pyridin-3-yloxy)-isoquinoline-3-carboxylic acid ethyl esterHCID 178418546HCID 178418546、化合物

生成物 1

HCID 898130801-Cyano-4-hydroxy-7-(pyridin-3-yloxy)-isoquinoline-3-carboxylic acid ethyl ester収率 32.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

A mixture of 4-hydroxy-1-iodo-7-(pyridin-3-yloxy)-isoquinoline-3-carboxylic acid ethyl ester (215 mg) and CuCN (89 mg) in NMP (2 mL) was heated at 120° C. for 2 h; the reaction was then cooled, diluted with DCM, and stirred at rt overnight; then diluted HCl solution was added and stirred for 1 h; the solids were filtered off, and DCM phase was separated, washed with water, and dil. NaCl solution, dried over anhydrous sodium sulphate, filtered, concentrated and the residue was column purified to give product (53 mg). LCMS ESI+: 336 (M+1)+.

後処理

  1. temperaturethe reaction was then cooled
  2. stirringstirred for 1 h
  3. filtrationthe solids were filtered off
  4. customDCM phase was separated
  5. washwashed with water, and dil. NaCl solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified

出典と根拠

ORDレコード
ord-d61d45dc6b6c4c4da257ccfbc638c66c
出典データセット
uspto-grants-2016_08
特許番号
US09409892B2

反応ノート

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