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

HRID 1094600Notes

Reaction equation

HRID 1094600 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-edc885920a9d41e0b025fa1525c563e5
Source dataset
uspto-grants-2012_03
Patent number
US08133992B2

Reaction notes

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