Dimethylformamide → HCID 69091337, compound

HRID 705041Notes

Reaction equation

HRID 705041 reaction equation
CN(C=O)C.[F:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:17]=[CH:16][NH:15][N:14]=2)[CH:10]=[N:11][CH:12]=1.Br[C:19]1[N:24]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3].O>[F:6][C:7]1[CH:8]=[C:9]([C:13]2[CH:17]=[CH:16][N:15]([C:19]3[N:24]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=[CH:21][CH:20]=3)[N:14]=2)[CH:10]=[N:11][CH:12]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 16217886Methyl 6-bromopyridine-2-carboxylateHCID 178505992HCID 178505992, compound

Product 1

HCID 69091337HCID 69091337, compound

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 5483663Ferric acetylacetonateCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

30 ml of DMF were added to 1.88 g (11.5 mmol) of 3-(5-fluoro-3-pyridinyl)-1H-pyrazole (preparation cf. step 2), 2.50 g (11.5 mmol) of methyl 6-bromo-2-pyridinecarboxylate, 92.0 mg (1.15 mmol) of copper (II) oxide, 7.54 g (23.10 mmol) of cesium carbonate and 1.22 g (3.47 mmol) of iron(III) acetylacetonate, and the mixture was stirred at 90° C. for 60 hours. The entire reaction mixture was then cooled to room temperature, and water was added. The reaction mixture was then extracted with ethyl acetate. The organic phase was separated off, dried, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel. This gave 191 mg (5.0% of theory) of methyl 6-[3-(5-fluoro-3-pyridinyl)-1H-pyrazol-1-yl]-2-pyridinecarboxylate.

Workup

  1. customThe entire reaction mixture
  2. temperaturewas then cooled to room temperature
  3. extractionThe reaction mixture was then extracted with ethyl acetate
  4. customThe organic phase was separated off
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-51486ae8918c4204a8b3eccbcd06da05
Source dataset
uspto-grants-2015_11
Patent number
US09173396B2

Reaction notes

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