Ethanol → 3-(2-Carboxyethyl)-4,6-dibromo-1H-indole-2-carboxylic acid

HRID 1950677ノート

反応式

HRID 1950677 の反応式
[Br:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[C:7]2[C:3]=1[C:4]([CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[C:5]([C:12]([O:14]CC)=[O:13])[NH:6]2.O.O.O.[OH-].[Li+].C(O)C.C(OCC)(=O)C>O1CCCC1.O.CO.CCCCCC>[C:19]([CH2:18][CH2:17][C:4]1[C:3]2[C:7](=[CH:8][C:9]([Br:11])=[CH:10][C:2]=2[Br:1])[NH:6][C:5]=1[C:12]([OH:14])=[O:13])([OH:21])=[O:20]

参加物

9

反応物 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 71280731ethyl 4,6-dibromo-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylateHCID 86677587Lithium hydroxide trihydrate

生成物 1

HCID 712808663-(2-Carboxyethyl)-4,6-dibromo-1H-indole-2-carboxylic acid収率 95%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

Ethyl 4,6-dibromo-3-(3-ethoxy-3-oxopropyl)-1H-indole-2-carboxylate (4.47 g, 10 mmol) was dissolved in 25 ml tetrahydrofurane (THF) with stirring at rt. Then a solution of 1.26 g of lithium hydroxide trihydrate (3 equiv.) in 25 ml water was added and the resulting mixture was let to stir at rt for 24 h. After completion of the reaction THF was removed under reduced pressure and the pH was adjusted to 4-5, and the product was extracted with diethyl ether (3×30 ml). The organic layers were dried over magnesium sulfate, filtered, and evaporated to dryness to yield a light-beige-colored solid in 95-100% yield. mp. 259° C.; well soluble in methanol, ethanol and ethyl acetate; slightly soluble in petrol ether, water, hexane. 1H-NMR (MeOH-d4): δ 2.67 (t, 2H, 3J=8.4 Hz, CH2); 3.71 (t, 2H, 3J=8.4 Hz, CH2); 7.42 (d, 1H, 4J=1.6 Hz, C7-H); 7.62 (d, 1H, 4J=1.6 Hz, C5-H). 13C-NMR (MeOH-d4): δ 21.4 (C-2′); 37.9 (C-1′); 115.9 (C-7); 117.0 (C-4); 118.8 (C-6); 123.9 (C-3); 125.5 (C-2); 127.9 (C-3a); 128.2 (C-5); 139.6 (C-7a); 164.6 (2′-CO2H); 170.1 (2-CO2H). LC-MS (m/z): 392.0 [M]+; 390.0 [M]−. Purity (LC-MS): 99%.

後処理

  1. stirringto stir at rt for 24 h
  2. customwas removed under reduced pressure
  3. extractionthe product was extracted with diethyl ether (3×30 ml)
  4. dry with materialThe organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customto yield a light-beige-colored solid in 95-100% yield

出典と根拠

ORDレコード
ord-3770e0d8e4a7449ebddbdc7239a95d6b
出典データセット
uspto-grants-2013_03
特許番号
US08404436B1

反応ノート

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