Water → HCID 23090154, compound

HRID 1437262Notes

Reaction equation

HRID 1437262 reaction equation
[CH3:1][O-:2].[Na+].C([O:6][C:7]([C:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:11]([C:20]2[CH:25]=[CH:24][C:23](Br)=[CH:22][N:21]=2)[N:10]=1)=[O:8])C.O>CO.C1(C)C=CC=CC=1.[Cu]Br>[CH3:1][O:2][C:23]1[CH:24]=[CH:25][C:20]([N:11]2[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)=[CH:13][C:9]([C:7]([OH:6])=[O:8])=[N:10]2)=[N:21][CH:22]=1

Participants

7

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 23143431HCID 23143431, compound

Product 1

HCID 23090154HCID 23090154, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

In an argon atmosphere at room temperature, sodium methoxide (1.74 g) and copper(I) bromide (0.231 g) were added to the above-obtained 1-(5-bromo-2-pyridyl)-5-(2-pyridyl)pyrazole-3-carboxylic acid ethyl ester (3.00 g) in a mixture of methanol (30 mL) and toluene (30 mL). The resultant mixture was refluxed under heat for 47 hours, and then cooled in air. Water (50 mL) was added to the reaction mixture, followed by stirring at room temperature for 1.5 hours. The reaction mixture was partitioned by use of water, acetic acid (10 mL), and methanol-chloroform (1:10) solvent mixture. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, to thereby give the title compound as a solid (1.68 g, 71%).

Workup

  1. temperatureunder heat for 47 hours
  2. temperaturecooled in air
  3. customThe reaction mixture was partitioned by use of water, acetic acid (10 mL), and methanol-chloroform (1:10) solvent mixture
  4. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  5. filtrationfollowed by filtration
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-86f68c64a1d24cfc90ea357eaafa1619
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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