Ammonium Chloride → HCID 86692492, compound

HRID 1748540Notes

Reaction equation

HRID 1748540 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH3:19]B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>O1CCOCC1.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:19])=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 46739344Ethyl 1-(5-bromopyridin-2-yl)-5-methylpyrazole-4-carboxylate

Product 1

HCID 86692492HCID 86692492, compoundYield 88.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 12976736Bis(ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane);iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A suspension of 1-(5-bromopyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (4 g) in Reference Example 24 (2), methylboronic acid (1.54 g), 1,1′-bis(di-tert-butylphosphino)ferrocene (306 mg), palladium acetate (145 mg) and tripotassium phosphate (11 g) in 1,4-dioxane (30 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 ethyl acetate. 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 5-methyl-1-(5-methylpyridin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (2.81 g) as a white solid. MS (ESI) m/z: 246 (M+H)+.

Workup

  1. temperatureunder reflux
  2. customAfter completion of the reaction
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  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-0559587b64cf43fb81a0ee4ee9b23529
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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