2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 57559126, compound

HRID 37962Notes

Reaction equation

HRID 37962 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([N:8]2[CH2:21][CH2:20][C:19]3[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[NH:12][C:11]=3[C:10]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:9]2)=[O:7])=[CH:4][CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=[O:37])C=1Cl>C1COCC1.O>[CH2:25]([O:24][C:22]([C:10]1[C:11]2[NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:19]=2[C:20](=[O:37])[CH2:21][N:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:28][CH:27]=2)[CH:9]=1)=[O:23])[CH3:26]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone2×HCID 25121533Ethyl 3-(4-fluorobenzoyl)-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate

Product 1

HCID 57559126HCID 57559126, compoundYield 92%

Reagents, catalysts & solvents 1

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

Procedure

To a mixture of ethyl 3-(4-fluorobenzoyl)-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate (190 mg, 0.5 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (139 mg, 0.6 mmol) was added a mixture of THF—H2O (9:1, 8 mL) at ambient temperature. The reaction mixture was allowed to stir at ambient temperature for 2 hours. Additional DDQ (139 mg, 0.6 mmol) was added, and the mixture was stirred at ambient temperature for another 2 hours. The solvent was removed in vacuo, and the residue was taken up in EtOAc and washed thoroughly with saturated sodium bicarbonate solution and then with brine. The organic phase was dried with sodium sulfate, and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with hexane-EtOAc (85:15) to give the title compound as a yellow solid (180 mg, 92%); 1H-NMR (CDCl3): δ 11.4 (1H, s), 8.52-8.48 (2H, m), 7.66-7.62 (2H, m), 7.48-7.46 (1H, m), 7.37-7.31 (2H, m), 7.22-7.17 (2H, m), 4.53 (2H, s), 4.38 (2H, q), 1.35 (3H, t); MS (ES): 393 (MH+).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at ambient temperature for another 2 hours
  3. customThe solvent was removed in vacuo
  4. washwashed thoroughly with saturated sodium bicarbonate solution
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel eluting with hexane-EtOAc (85:15)

Sources & evidence

ORD record
ord-398b8ffd1155427b881e2d3bbd5e44e1
Source dataset
uspto-grants-2013_09
Patent number
US08524704B2

Reaction notes

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