2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 89783941, compound

HRID 1056050Notes

Reaction equation

HRID 1056050 reaction equation
[O:1]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:18]3[NH:26][C:25]4[CH2:24][CH2:23][NH:22][C:21](=[O:27])[C:20]=4[CH:19]=3)[CH:12]=[CH:13][CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[O:1]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:18]3[NH:26][C:25]4[CH:24]=[CH:23][NH:22][C:21](=[O:27])[C:20]=4[CH:19]=3)[CH:12]=[CH:13][CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 89784005HCID 89784005, compound

Product 1

HCID 89783941HCID 89783941, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(2-phenoxyquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 37; 0.07 g, 0.197 mmol) in 1,4-dioxane (20 mL) was added DDQ (0.134 g, 0.591 mmol), and the reaction was stirred at RT for 2.5 h. The mixture was diluted with ice water (50 mL) and extracted with EtOAc (50 mL). The organic layer was separated, dried, filtered and concentrated. The residue was purified with preparative HPLC (Phenomenex Gemini C18 column (100×50 mm, 10 μm), 90 mL/min, 30-90% ACN in water with 0.1% TFA) to give 2-(2-phenoxyquinolin-8-yl)-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.034 g, 49%) as a pale brown solid. MS (ESI, pos. ion) m/z: 354.1 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 11.28 (s, 1H), 10.73 (d, 1H, J=5.2 Hz), 8.54 (d, 1H, J=8.9 Hz), 8.31 (d, 1H, J=7.1 Hz), 7.89 (d, 1H, J=7.6 Hz), 7.67 (t, J=7.8 Hz, 2H), 7.54 (t, J=7.6 Hz, 2H), 7.44-7.47 (m, 3H), 7.24 (d, 1H, J=1.3 Hz), 6.90-7.03 (m, 1H), 5.87 (d, 1H, J=7.0 Hz).

Workup

  1. extractionextracted with EtOAc (50 mL)
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with preparative HPLC (Phenomenex Gemini C18 column (100×50 mm, 10 μm), 90 mL/min, 30-90% ACN in water with 0.1% TFA)

Sources & evidence

ORD record
ord-fe71a4ccb5a54d068f12302700273c67
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…