Dimethylformamide → Ethyl 6-chloro-3-formyl-1H-indole-2-carboxylate

HRID 555703노트

반응식

HRID 555703 반응식
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([Cl:15])[CH:9]=2)=[O:5])[CH3:2].O=P(Cl)(Cl)Cl.CN([CH:24]=[O:25])C>>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH:24]=[O:25])=[CH:12][CH:11]=[C:10]([Cl:15])[CH:9]=2)=[O:5])[CH3:2]

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 7015027Ethyl 6-chloroindole-2-carboxylate

생성물 1

HCID 4591751Ethyl 6-chloro-3-formyl-1H-indole-2-carboxylate

실험 절차

The title compound is prepared according to a published literature procedure (see J. Med. Chem. 2005, 48, 995-1018.) A solution of 6-chloro-1H-indole-2-carboxylic acid ethyl ester (5.0 g, 22.4 mmol) (commercially available from 3D Medical Systems Inc.) and POCl3 (2.46 mL, 26.8 mmol) in DMF (15 mL) is heated at 50° C. for 28 h. After completion, the reaction mixture is quenched by aqueous NaHCO3, Et2O is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords the title compound as a colorless powder; ES-MS: M−=250.1; HPLC: AtRet=4.67 min.

후처리

  1. customThe title compound is prepared
  2. customAfter completion, the reaction mixture is quenched by aqueous NaHCO3, Et2O
  3. additionis added
  4. washthe organic layer is washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-edddfaa76c1a43fa9465d9979a14a87e
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053457B2

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