4-Fluorophenol → HCID 58167957, compound

HRID 1029120Notes

Reaction equation

HRID 1029120 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=1[C:6](=[O:12])[NH:7]2.F[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.[C:25](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[C:4]2[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=2[C:6](=[O:12])[NH:7]3)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 58167957HCID 58167957, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1-Chloro-5H-benzo[c][1,8]naphthyridin-6-one (50 mg, 0.22 mmol), 4-fluorophenol (73 mg, 0.65 mmol), and potassium carbonate (150 mg, 1.08 mmol) were suspended in DMF (2 mL), and stirred overnight at 100° C. The reaction solution was cooled to room temperature, diluted with H2O, and the resulting precipitate was filtered. The precipitate was washed with H2O, and dried under vacuum to provide 149 (14 mg, 21% yield) as a tan solid. LC-MS (M+H=307, obsd.=307). 1H NMR (400 MHz, d6-DMSO): δ 12.15 (s, 1H), 9.05 (d, 1H), 8.42 (dd, 1H), 8.29 (d, 1H), 7.88 (dt, 1H), 7.71 (t, 1H), 7.40 (m, 4H), 6.52 (d, 1H).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationthe resulting precipitate was filtered
  3. washThe precipitate was washed with H2O
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4f2f99b0414044acb08dcf623c9849d9
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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