Cesium carbonate → 1-(4-Amino-2-fluoro-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

HRID 1029146Notes

Reaction equation

HRID 1029146 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.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([F:25])[CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][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)=[C:20]([F:25])[CH:19]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2735918Phenol, 4-amino-2-fluoro-HCID 581680081-Chlorobenzo[C][1,8]naphthyridin-6(5H)-one

Product 1

HCID 581683451-(4-Amino-2-fluoro-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-oneYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Compound 83 (250 mg, 1.08 mmol), 4-amino-2-fluoro-phenol (276 mg, 2.17 mmol), and cesium carbonate (1.41 g, 4.34 mmol) were suspended in DMF (5 mL), and stirred for 30 minutes at 120° C. in microwave. The reaction mixture was diluted with H2O. The resulting precipitate was filtered. The precipitate was tritturated with MeOH, filtered, washed with MeOH, and dried under vacuum to provide 182 (312 mg, 90% yield) as a solid. LC-MS (M+H=322, obsd.=322).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. filtrationfiltered
  3. washwashed with MeOH
  4. customdried under vacuum

Sources & evidence

ORD record
ord-2a5d788b0d094b169f97d9ee159d4f00
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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