Indoline → HCID 18629224、化合物

HRID 1271152ノート

反応式

HRID 1271152 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Br-:10].[Br-:11].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[Br:10][C:6]1[CH:5]=[C:4]2[C:9](=[C:8]([Br:11])[CH:7]=1)[NH:1][CH2:2][CH2:3]2

参加物

4

反応物 2

HCID 10328IndolineHCID 21124087Pyridiniumtribromide

生成物 1

HCID 18629224HCID 18629224、化合物収率 84.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Part A: Indoline (2.2 g, 18.04 mmol), dissolved in dichloromethane (160 mL) was stirred with pyridinium tribromide (12 g, 37.6 mmol) for 16 h at 25° C. The reaction was quenched with sat NaHSO3 (50 mL) and water (50 mL). The dichloromethane was separated, dried (MgSO4) and stripped in vacuo. The residue was chromatographed on silica gel using 20% ethyl acetate/hexanes as eluent to give 5,7-dibromoindoline (4.2 g, 84% yield). 1H NMR(CDCl3) δ 7.28 (m, 1H), 7.11 (s, 1H), 3.96 (s br, 1H ), 3.63 (t J=9 Hz, 1H), 3.13 (t J=9 Hz, 2H).

後処理

  1. customThe reaction was quenched with sat NaHSO3 (50 mL) and water (50 mL)
  2. customThe dichloromethane was separated
  3. dry with materialdried (MgSO4)
  4. customThe residue was chromatographed on silica gel using 20% ethyl acetate/hexanes as eluent

出典と根拠

ORDレコード
ord-76f19e53dee44d659a2d4af7c775bd0e
出典データセット
uspto-grants-2007_04
特許番号
US07205306B2

反応ノート

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