2,2'-Bipyridine → HCID 59645219, compound

HRID 2252809Notes

Reaction equation

HRID 2252809 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[C:7](Br)[N:6]=1)=[O:4].[S:27]([C:31]1C=CC(C)=CC=1)([O-])(=[O:29])=[O:28].[N:38]1C=CC=C[C:39]=1C1C=CC=CN=1>[Cu-]=O.CN(C=O)C>[CH3:39][N:38]([S:27]([CH3:31])(=[O:29])=[O:28])[C:7]1[N:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:14]([O:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2

Participants

6

Reactant 3

HCID 14742,2'-BipyridineHCID 85570p-ToluenesulfonateHCID 11339571Methyl 5-bromo-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate

Product 1

HCID 59645219HCID 59645219, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

In a dried sealable pressure tube flushed with nitrogen was placed methyl 5-bromo-8-{[(4-methylphenyl)sulfonyl]oxy}-1,6-naphthyridine-7-carboxylate (500 mg, 1.14 mmol, prepared as described in Example 2, Step 2), N-methylmethanesulfonamide (168 mg, 1.54 mmol, prepared as in J. Chem. Soc., Perkins Trans. 1986, 2 (8): 1211-16), 2,2′-bipyridyl (241 mg, 1.54 mmol), dry DMF (3 mL) and copper(I) oxide (221 mg, 1.54 mmol). The tube was capped and heated to 85° C. overnight. In the morning, the reaction was cooled and filtered through a glass fiber filter, washing with chloroform. The filtrate was diluted with chloroform (about 100 mL total volume) and stirred with an EDTA solution (5 g EDTA in 100 mL water) for two hours or until the aqueous layer became aqua in color and the organic layer became yellow. The layers were separated and the aqueous layer was extracted twice more with chloroform. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (ISCO column, 110 g silica) eluting with a 0-5% MeOH/CHCl3 gradient over 35 minutes. The concentrated fractions were triturated with methanol to give the product as a white solid.

Workup

  1. customIn a dried sealable pressure tube flushed with nitrogen
  2. customThe tube was capped
  3. temperatureIn the morning, the reaction was cooled
  4. filtrationfiltered through a glass fiber
  5. filtrationfilter
  6. washwashing with chloroform
  7. additionThe filtrate was diluted with chloroform (about 100 mL total volume)
  8. customThe layers were separated
  9. extractionthe aqueous layer was extracted twice more with chloroform
  10. dry with materialThe combined organic extracts were dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by flash column chromatography (ISCO column, 110 g silica)
  14. washeluting with a 0-5% MeOH/CHCl3 gradient over 35 minutes
  15. customThe concentrated fractions were triturated with methanol

Sources & evidence

ORD record
ord-fc341686d07c412792c6e436046df3d0
Source dataset
uspto-grants-2008_01
Patent number
US07323460B2

Reaction notes

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