Dimethylformamide → Ethyl3-Formyl-2-isopropyl-1H-indole-6-carboxylate

HRID 40060ノート

反応式

HRID 40060 の反応式
[CH:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=2)([CH3:3])[CH3:2].O=P(Cl)(Cl)Cl.CN([CH:26]=[O:27])C>>[CH:26]([C:12]1[C:11]2[C:6](=[CH:7][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:10]=2)[NH:5][C:4]=1[CH:1]([CH3:3])[CH3:2])=[O:27]

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 59762345Ethyl2-Isopropyl-1H-indole-6-carboxylate2 回

生成物 1

HCID 59762423Ethyl3-Formyl-2-isopropyl-1H-indole-6-carboxylate

反応条件

温度
25 °C

実験手順

To a solution of ethyl 2-isopropyl-1H-indole-6-carboxylate (Compound 33, 2.00 g, 8.66 mmol) in DMF (12 ml) at 0° C. under argon then added dropwise POCl3 (1.58 ml, 17.3 mmol) was added dropwise. The reaction was stirred for 30 minutes at 25° C. then cooled to 0° C., quenched with saturated NaHCO3, diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound as a light tan solid.

後処理

  1. additionwas added dropwise
  2. temperaturethen cooled to 0° C.
  3. customquenched with saturated NaHCO3
  4. additiondiluted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

出典と根拠

ORDレコード
ord-3d7cd3c0fcc74d7cb5299da3226f7c16
出典データセット
uspto-grants-2013_09
特許番号
US08524917B2

反応ノート

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