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

HRID 402816

反応式

HRID 402816 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 772301786-methoxy-1-(propan-2-yl)-1H-indole-3-carbaldehyde収率 87.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Cesium carbonate (558 mg, 1.71 mmol) was added to a stirred room temperature of 6-methoxy-1H-indole-3-carbaldehyde (100 mg, 0.57 mmol) in DMF (1.0 mL) and the mixture was stirred at room temperature for 15 minutes. Then 2-iodopropane (0.114 mL, 1.14 mmol) was added and the solution was stirred for 80° C. for 2 hours. The solution was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (2×15 mL) and saturated sodium bicarbonate (5 mL), washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude title intermediate (108 mg).

後処理

  1. stirringthe solution was stirred for 80° C. for 2 hours
  2. concentrationThe solution was concentrated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate (2×15 mL) and saturated sodium bicarbonate (5 mL)
  4. washwashed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-659b8288bf354e9297588a86b7d09714
出典データセット
uspto-grants-2014_06
特許番号
US08742110B2

関連ノート

読み込み中…