Indoline → HCID 18629224, compound

HRID 1271152Notes

Reaction equation

HRID 1271152 reaction equation
[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

Participants

4

Reactant 2

HCID 10328IndolineHCID 21124087Pyridiniumtribromide

Product 1

HCID 18629224HCID 18629224, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-76f19e53dee44d659a2d4af7c775bd0e
Source dataset
uspto-grants-2007_04
Patent number
US07205306B2

Reaction notes

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