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

HRID 2214751

반응식

HRID 2214751 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 219483751-Acetyl-6-bromo-5-methoxyindoline수율 88.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5f997226f28c48008664d4de881b219d
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109201B2

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