Potassium Phosphate, Tribasic → HCID 86692440, compound

HRID 1748471Notes

Reaction equation

HRID 1748471 reaction equation
C(B1O[C:8]([CH3:10])([CH3:9])[C:5]([CH3:7])(C)O1)=C.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:20]([O:22][C:23]([C:25]1[CH:26]=[N:27][N:28]([C:31]2[C:36]([Cl:37])=CC(Br)=C[N:32]=2)[C:29]=1[CH3:30])=[O:24])[CH3:21]>CN(C)C=O.O>[CH2:20]([O:22][C:23]([C:25]1[CH:26]=[N:27][N:28]([C:31]2[C:36]([Cl:37])=[CH:9][C:8]([CH:5]=[CH2:7])=[CH:10][N:32]=2)[C:29]=1[CH3:30])=[O:24])[CH3:21]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86692432HCID 86692432, compound

Product 1

HCID 86692440HCID 86692440, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Vinylboronic acid pinacol ester (1.37 ml), tripotassium phosphate (3.85 g) and 1,1′-bis(diphenylphosphino)ferrocene-palladium (II) dichloride dichloromethane complex (301 mg) were added to a solution of 1-(5-bromo-3-chloropyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (2.52 g) described in Reference Example 44(2) in N,N-dimethylformamide (36 ml), and the mixture was stirred at 100° C. for seven hours. The reaction solution was cooled to room temperature, diluted with water, filtered through Celite and the filtrate was extracted with ethyl acetate three times. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-(3-chloro-5-vinylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.67 g).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationfiltered through Celite
  3. extractionthe filtrate was extracted with ethyl acetate three times
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-21c6633b16914ec08cef947ec6dbfe12
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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