Indoline → HCID 18629224, compound

HRID 2251017Notes

Reaction equation

HRID 2251017 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-b527316b9a1245d59c6fab5d492dd61e
Source dataset
uspto-grants-2008_01
Patent number
US07319100B2

Reaction notes

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