3-Chlorophenol → HCID 58168186, compound

HRID 1029095Notes

Reaction equation

HRID 1029095 reaction equation
F[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.Cl[C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1.[C:25](=O)([O-])[O-:26].[K+].[K+]>CN(C=O)C>[CH3:25][O:26][C:23]1[CH:22]=[CH:21][C:20]([O:24][C:2]2[CH:16]=[CH:15][C:5]3[C:6](=[O:14])[NH:7][C:8]4[C:13]([C:4]=3[CH:3]=2)=[CH:12][CH:11]=[CH:10][N:9]=4)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 79333-ChlorophenolHCID 11430Potassium CarbonateHCID 58168117HCID 58168117, compound

Product 1

HCID 58168186HCID 58168186, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

9-Fluoro-5H-benzo[c][1,8]naphthyridin-6-one (40 mg, 0.19 mmol), 3-chlorophenol (72 mg, 0.56 mmol), and potassium carbonate (129 mg, 0.93 mmol) were suspended in DMF (1.5 mL), and stirred for 20 minutes at 180° C. in the microwave. The reaction mixture was quenched with H2O. The resulting precipitate was filtered, washed with H2O, and dried under vacuum to provide 73 (50 mg, 83% yield) as a tan solid. LC-MS (M+H=323, obsd.=323). 1H NMR (400 MHz, d6-DMSO): δ 12.05 (s, 1H), 8.78 (dd, 1H), 8.51 (dd, 1H), 8.35 (d, 1H), 8.19 (d, 1H), 7.49 (t, 1H), 7.29 (m, 4H), 7.12 (dd, 1H).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with H2O
  4. customdried under vacuum

Sources & evidence

ORD record
ord-895854ec5ff44da28bb45fd29c8e6d1e
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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