2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 59848835, compound

HRID 1096501Notes

Reaction equation

HRID 1096501 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13][C:3]([C:4]=23)=[CH:2]1.ClC1C(=O)C(C#N)=C(C#N)C(=[O:29])C=1Cl>C1COCC1.O>[O:29]=[C:13]1[C:3]2=[CH:2][NH:1][C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([C:4]=32)[CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 59848834HCID 59848834, compound

Product 1

HCID 59848835HCID 59848835, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

tert-butyl 1,3,4,6-tetrahydro-5H-azepino[5,4,3-cd]indole-5-carboxylate, Intermediate 12 (100 mg, 0.37 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (167 mg, 0.73 mmol) in THF/water 9/1 (8 ml) was stirred under N2 over night at room temperature. The compound was purified on a Biotage preparative flash column eluting with 15-100% EtOAc in petroleum ether 40-65° C. Obtained 58 mg of the title compound. MS (ESI+) m/z 231 [M+H-isobutene]+.

Workup

  1. customThe compound was purified on a Biotage preparative flash column
  2. washeluting with 15-100% EtOAc in petroleum ether 40-65° C

Sources & evidence

ORD record
ord-e9c068886d5a442dbb71a857497239dd
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

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