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3-Hydroxypyridine → 2-{[(2,4-Dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-4-(pyridin-3-yloxy)-benzoic acid ethyl ester

HRID 1480972
ノート
印刷プレビュー

反応式

HRID 1480972 の反応式
[CH2:1]([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][C:6]=1[CH2:12][N:13](OC1C=CC(OC)=CC=1OC)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:2].[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([OH:38])[CH:33]=1.C[C:40]([CH3:51])([C:42](=O)[CH2:43][C:44](=[O:49])[C:45]([CH3:48])(C)C)C.[C:52](=[O:55])([O-])[O-].[Cs+].[Cs+].[CH3:58]N1C(=O)CCC1>CCOC(C)=O.Cl[Cu]>[CH2:1]([O:3][C:4](=[O:31])[C:5]1[CH:10]=[CH:9][C:8]([O:38][C:34]2[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=2)=[CH:7][C:6]=1[CH2:12][N:13]([CH2:51][C:40]1[CH:42]=[CH:43][C:44]([O:49][CH3:58])=[CH:45][C:48]=1[O:55][CH3:52])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:2]
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 5

HCID 79713-HydroxypyridineHCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 898132434-Bromo-2-{[(2,4-dimethoxy-phenoxy)-ethoxycarbonylmethyl-amino]-methyl}-benzoic acid ethyl ester

生成物 1

HCID 89813094
2-{[(2,4-Dimethoxy-benzyl)-ethoxycarbonylmethyl-amino]-methyl}-4-(pyridin-3-yloxy)-benzoic acid ethyl ester

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

A mixture of 4-bromo-2-{[(2,4-dimethoxy-phenoxy)-ethoxycarbonylmethyl-amino]-methyl}-benzoic acid ethyl ester (3.292 g), pyridin-3-ol (887 mg), CuCl (330 mg), 2,2,6,6-tetramethyl-heptane-3,5-dione (TMHD, 0.26 mL), cesium carbonate (3.26 g) in NMP (6 mL) was heated at 130° C. for 24 h. Then the reaction was cooled, diluted with EtOAc, solids were filtered off, filtrate was washed with water, diluted NaCl solution, dried over sodium sulfate, filtered off, concentrated; the residue was column purified to give the desired product (1.71 g). LC MS ESI+: 509 (M+1)+.

後処理

  1. temperatureThen the reaction was cooled
  2. filtrationwere filtered off
  3. washfiltrate was washed with water, diluted NaCl solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated
  7. custompurified

出典と根拠

ORDレコード
ord-5d9be79dc7264d8fb8ea3c70d1926b75
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409892B2

反応ノート

読み込み中…

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