Potassium Carbonate → HCID 58168329, compound

HRID 1029105Notes

Reaction equation

HRID 1029105 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.[Br:17][C:18]1[CH:19]=[C:20](O)C=[CH:22][CH:23]=1.[C:25](=[O:28])([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[Br:17][C:18]1[CH:19]=[CH:20][C:25]([O:28][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:22][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 58168117HCID 58168117, compound

Product 1

HCID 58168329HCID 58168329, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
200 °C

Procedure

9-Fluoro-5H-benzo[c][1,8]naphthyridin-6-one (40 mg, 0.19 mmol), 3-bromophenol (97 mg, 0.56 mmol), and potassium carbonate (129 mg, 0.93 mmol) were suspended in dimethylacetamide (2 mL), and stirred for 30 minutes at 200° 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 93 (2 mg, 3% yield) as a solid. LC-MS (M+H=367, obsd.=367). 1H NMR (400 MHz, d6-DMSO): δ 12.01 (s, 1H), 8.78 (d, 1H), 8.52 (d, 1H), 8.35 (d, 1H), 8.22 (d, 1H), 7.43 (m, 3H), 7.29 (m, 2H), 7.18 (m, 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-23d6bd001986418c93aa140828ec3aac
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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