Acetic Acid → 6-Ethyl-3-formyl-indole-1-carboxylic acid amide

HRID 1527165ノート

反応式

HRID 1527165 の反応式
[H-].[Na+].[CH2:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:14]=[O:15])=[CH:10][NH:11]2)=[CH:7][CH:6]=1)[CH3:4].ClS([N:20]=[C:21]=[O:22])(=O)=O.C(O)(=O)C>C1COCC1.O>[CH2:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:14]=[O:15])=[CH:10][N:11]2[C:21]([NH2:20])=[O:22])=[CH:7][CH:6]=1)[CH3:4]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 70918Chlorosulfonyl isocyanateHCID 218501566-Ethyl-1H-indole-3-carbaldehyde

生成物 1

HCID 866737906-Ethyl-3-formyl-indole-1-carboxylic acid amide

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
5 °C

実験手順

To a solution of NaH (60% in mineral oil, 259 mg, 6.47 mmol) in THF (10 mL) cooled to 5° C. under nitrogen a solution of 6-ethyl-1H-indole-3-carbaldehyde (1.12 g, 6.47 mmol) in THF (20 mL) was slowly added and the mixture was stirred at 5° C. for 30 min. While maintaining the internal temperature between 5° C. and 10° C., chlorosulfonyl isocyanate (1.12 mL, 12.9 mmol) was added dropwise and the solution was further stirred at RT overnight. Acetic acid (15 mL) was added (slightly exothermic) and the solution was stirred at RT for 1.5 h. Ice cubes and water (25 mL) were added, and the solution was further stirred at RT for 30 min. Water was added and the mixture was extracted with EtOAc. The aqueous layer was back-extracted twice with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to EtOAc) to give the desired compound. LC/MS: 290.0 [M+H]+, 312.0 [M+Na]+; tR (HPLC conditions a): 3.02 min.

後処理

  1. additionwas slowly added
  2. additionwas added dropwise
  3. stirringthe solution was further stirred at RT overnight
  4. stirringwas stirred at RT for 1.5 h
  5. stirringthe solution was further stirred at RT for 30 min
  6. extractionthe mixture was extracted with EtOAc
  7. extractionThe aqueous layer was back-extracted twice with EtOAc
  8. dry with materialThe combined organic layers were dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to EtOAc)

出典と根拠

ORDレコード
ord-e9b12aa64ae5409a83b0072d063a41df
出典データセット
uspto-grants-2015_07
特許番号
US09085555B2

反応ノート

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