2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-(4-methoxyphenyl)-6-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide

HRID 2410660Notes

Reaction equation

HRID 2410660 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:19](=[C:20]([C:22]([NH2:24])=[O:23])[CH:21]=2)[NH:18][C:17]2[CH2:16][CH2:15][CH:14]([C:25]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[O:26])[CH2:13][C:12]3=2)=[CH:5][CH:4]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:21]=[C:20]([C:22]([NH2:24])=[O:23])[C:19]3[NH:18][C:17]4[C:12]([C:11]=3[CH:10]=2)=[CH:13][C:14]([C:25]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:26])=[CH:15][CH:16]=4)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 468324406-(4-methoxyphenyl)-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide

Product 1

HCID 468324413-(4-methoxyphenyl)-6-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamideYield 49.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred suspension of 6-(4-methoxyphenyl)-3-(morpholine-4-carbonyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (6 mg, 0.014 mmol, Example 1) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (9.43 mg, 0.042 mmol) in toluene (2 mL) was heated at reflux for 2 h. The reaction mixture was concentrated, and the crude was purified by prep. HPLC to afford 3 mg of 3-(4-methoxyphenyl)-6-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide. MS (ESI) m/z 430.2 (M+H). 1H NMR (DMSO-d6) δ ppm 11.50 (s, 1H) 8.63 (s, 1H) 8.30 (s, 2H) 8.16-8.24 (m, 1H) 7.77 (d, J=8.79 Hz, 2H) 7.69 (d, J=8.35 Hz, 1H) 7.49 (br. s., 1H) 7.38-7.44 (m, 1H) 7.01 (d, J=8.79 Hz, 2H) 3.76 (s, 3H) 3.55-3.61 (m, 4H) 3.48-3.55 (m, 4H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationThe reaction mixture was concentrated
  4. customthe crude was purified by prep

Sources & evidence

ORD record
ord-a9c1e57f5a534a6389ca1364481d7c89
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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