2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 69370348, compound

HRID 1861060Notes

Reaction equation

HRID 1861060 reaction equation
[CH:1]([C:9]1[C:17]2[CH2:16][CH2:15][C:14]([O:18][C:19]3[CH:20]=[C:21]([NH2:25])[CH:22]=[CH:23][CH:24]=3)=[CH:13][C:12]=2[NH:11][N:10]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(Cl)Cl.O1CCOCC1>[CH:1]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][C:19]3[CH:20]=[C:21]([NH:25][C:35](=[O:42])[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:22]=[CH:23][CH:24]=3)=[CH:15][CH:16]=2)[NH:11][N:10]=1)=[CH:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 693704203-(3-Styryl-4,5-dihydro-1H-indazol-6-yloxy)-phenylamine

Product 1

HCID 69370348HCID 69370348, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 3-(3-styryl-4,5-dihydro-1H-indazol-6-yloxy)-phenylamine (50 mg, 0.15 mmol) and N,N-diisopropylethylamine (54 μl, 0.31 mmol) in 5 mL of CH2Cl2, was added benzoyl chloride (36 μl, 0.31 mmol). After 15 min, the reaction mixture was diluted with CH2Cl2 and washed sequentially with 0.5N HCl, saturated sodium bicarbonate solution and brine, dried (MgSO4) and concentrated under reduced pressure. To a stirred solution of the residue in 1,4-dioxane was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (35 mg, 0.15 mmol). After 1 h, the reaction mixture was concentrated under reduced pressure and the residue was chromatographed on silica gel eluting hexanes/EtOAc (2:1). In this manner, N-[3-(2-benzoyl-3-styrl-1H-indazol-6-yloxy)-phenyl]-benzamide was prepared as a rust colored solid (90 mg, ˜quantitative): 1H NMR (CDCl3) δ 8.13 (s, 1H), 8.02 (d, 2H, J=7.0 Hz), 7.94 (d, 1H, J=8.7 Hz), 7.74 (d, 2H, J=6.8 Hz), 7.57-7.19 (m, 17H), 6.84 (d, 1H, J=8.3 Hz).

Workup

  1. washwashed sequentially with 0.5N HCl, saturated sodium bicarbonate solution and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. waitAfter 1 h
  5. concentrationthe reaction mixture was concentrated under reduced pressure
  6. customthe residue was chromatographed on silica gel
  7. washeluting hexanes/EtOAc (2:1)
  8. customIn this manner, N-[3-(2-benzoyl-3-styrl-1H-indazol-6-yloxy)-phenyl]-benzamide was prepared as a rust colored solid (90 mg, ˜quantitative)

Sources & evidence

ORD record
ord-2388a924e95a4b0ca4426f9f143654d7
Source dataset
uspto-grants-2003_03
Patent number
US06531491B1

Reaction notes

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