Sodium Carbonate → HCID 89662101, compound

HRID 1774520Notes

Reaction equation

HRID 1774520 reaction equation
[CH2:1]([N:8]1[C:12](OS(C(F)(F)F)(=O)=O)=[CH:11][C:10]([C:21]([O:23][CH3:24])=[O:22])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25]1(B(O)O)[CH2:27][CH2:26]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH2:1]([N:8]1[C:12]([CH:25]2[CH2:27][CH2:26]2)=[CH:11][C:10]([C:21]([O:23][CH3:24])=[O:22])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 89648955HCID 89648955, compound

Product 1

HCID 89662101HCID 89662101, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
75 °C

Procedure

2.57 g of methyl 1-benzyl-5-{[(trifluoromethyl)sulfonyl]oxy}-1H-pyrazole-3-carboxylate (7.06 mmol, 1.0 eq.) were dissolved in 51 mL of dry 1,2-dimethoxyethane under nitrogen atmosphere. 1.52 g of cyclopropylboronic acid (17.6 mmol, 2.5 eq.), 2.62 g of sodium carbonate (24.7 mmol, 3.5 eq.) and 408 mg of tetrakis(triphenylphosphin)palladium(0) (0.353 mmol, 0.05 eq.) were added and the mixture was stirred for 24 hours at 75° C. bath temperature. Then the mixture was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue purified by flash chromatography to give 1.61 g (5.39 mmol, 76%) of analytically pure target compound.

Workup

  1. filtrationThen the mixture was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue purified by flash chromatography
  5. customto give 1.61 g (5.39 mmol, 76%) of analytically pure target compound

Sources & evidence

ORD record
ord-cfa2ad9c59a5481b83000bd40120726c
Source dataset
uspto-grants-2016_02
Patent number
US09260412B2

Reaction notes

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