Ammonium Chloride → HCID 86692499, compound

HRID 1748551Notes

Reaction equation

HRID 1748551 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH:19]1(B(O)O)[CH2:21][CH2:20]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:13]=[N:14][C:15]([CH:19]3[CH2:21][CH2:20]3)=[CH:16][CH:17]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 86692500HCID 86692500, compound

Product 1

HCID 86692499HCID 86692499, compoundYield 55.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 1-(6-chloropyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.6 g), cyclopropylboronic acid (776 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (124 mg), palladium acetate (67.6 mg) and tripotassium phosphate (3.83 g) in 1,4-dioxane (13 ml) was stirred under reflux. After completion of the reaction, the mixture was allowed to cool, ice water and a saturated aqueous solution of ammonium chloride were added thereto, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. The obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give 1-(6-cyclopropylpyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (911 mg) as a brown oil. MS (ESI) m/z: 272 (M+H)+.

Workup

  1. temperatureunder reflux
  2. customAfter completion of the reaction
  3. temperatureto cool
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-461b45a23def491d9d77d7750eed2ab0
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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