Methyl iodide → 1-Acetyl-6-bromo-5-methoxyindoline

HRID 2214751

反応式

HRID 2214751 の反応式
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([OH:14])=[C:10]([Br:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:15]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:14][CH3:15])=[C:10]([Br:13])[CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 219483801-(6-Bromo-5-hydroxy-2,3-dihydro-1H-indol-1-yl)ethan-1-one

生成物 1

HCID 219483751-Acetyl-6-bromo-5-methoxyindoline収率 88.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A stirred solution of 1-acetyl-6-bromoindolin-5-ol (Tetrahedron 1973, 29(8), 1115; 40 g, 0.15 mole) in DMF (500 ml) was treated with K2CO3 (61 g, 0.45 mole) and iodomethane (11.7 ml, 0.19 mole) and maintained at room temperature for 20 h, then concentrated under vacuum to 200 ml. The residue was treated with water (200 ml) and the precipitate filtered off, dried and recrystallised from EtOAc to afford the title compound as a white solid (35.7 g, 85%). MH+ 270/272.

後処理

  1. concentrationconcentrated under vacuum to 200 ml
  2. additionThe residue was treated with water (200 ml)
  3. filtrationthe precipitate filtered off
  4. customdried
  5. customrecrystallised from EtOAc

出典と根拠

ORDレコード
ord-5f997226f28c48008664d4de881b219d
出典データセット
uspto-grants-2006_09
特許番号
US07109201B2

関連ノート

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