Isopropyl iodide → 6-methoxy-1-(propan-2-yl)-1H-indole-3-carbaldehyde

HRID 402814

반응식

HRID 402814 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:18]=[O:19])=[CH:14][NH:15]2)=[CH:11][CH:10]=1.I[CH:21]([CH3:23])[CH3:22]>CN(C=O)C>[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:18]=[O:19])=[CH:14][N:15]2[CH:21]([CH3:23])[CH3:22])=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 9072146-Methoxy-1H-indole-3-carboxaldehyde

생성물 1

HCID 772301786-methoxy-1-(propan-2-yl)-1H-indole-3-carbaldehyde수율 93.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

Cesium carbonate (577 mg, 1.77 mmol) was added to a stirred room temperature solution of 6-methoxy-1H-indole-3-carbaldehyde (104 mg, 0.590 mmol) in DMF (1.0 mL) and the mixture was stirred at room temperature for 15 minutes when 2-iodopropane (0.118 mg, 1.181 mmol) was added. The solution was stirred at 80° C. for 2 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate (2×20 mL) and saturated sodium bicarbonate (5 mL), washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated to give the title intermediate (120 mg).

후처리

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate (2×20 mL) and saturated sodium bicarbonate (5 mL)
  4. washwashed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c88445f42e054bc6a22df31aca2f613d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742110B2

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