2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Ethyl 5-bromo-1H-indole-7-carboxylate

HRID 656003Notes

Reaction equation

HRID 656003 reaction equation
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:24]=1)[NH:21][CH2:20][CH2:19]2>C(Cl)(Cl)Cl>[Br:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:24]=1)[NH:21][CH:20]=[CH:19]2

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 59332604Ethyl 5-bromoindoline-7-carboxylate

Product 1

HCID 59332585Ethyl 5-bromo-1H-indole-7-carboxylateYield 68,380.797%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

DDQ (119.3 g. 525.7 mmol) was added in several portions to a solution of ethyl 5-bromo-2,3-dihydro-1H-indole-7-carboxylate (129.1 g, 0.48 mmol) in CHCl3 (1500 mL) and the mixture was stirred for 2 h. The reaction was filtered and the solid was washed with CHCl3 (3×500 mL). The filtrate was washed with 5% NaOH (3×500 mL), H2O (500 mL) and brine (500 mL) then dried over Na2SO4. The solution was evaporated and the residue was recrystallized with EtOH, giving 88 g (69%) of the title compound.

Workup

  1. filtrationThe reaction was filtered
  2. washthe solid was washed with CHCl3 (3×500 mL)
  3. washThe filtrate was washed with 5% NaOH (3×500 mL), H2O (500 mL) and brine (500 mL)
  4. dry with materialthen dried over Na2SO4
  5. customThe solution was evaporated
  6. customthe residue was recrystallized with EtOH

Sources & evidence

ORD record
ord-8c507906e8db429abed27d614af095c7
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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