Potassium Carbonate → tert-Butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)acetate

HRID 1799000Notes

Reaction equation

HRID 1799000 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>CN(C)C(=O)C>[C:26]([O:25][C:23](=[O:24])[CH2:22][N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1)([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 59216326tert-Butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)acetateYield 77%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4,4,5,5-Tetramethyl-2-(1H-pyrazol-4-yl)-1,3,2-dioxaborolane (10 g), N,N-dimethylacetamide (100 ml), potassium carbonate (17.8 g) and t-butyl bromoacetate (9.9 ml) were mixed, and the mixture was stirred at room temperature for 4 hr. The reaction mixture was filtered through celite. Water and ethyl ether were added to the filtrate, and the mixture was partitioned in a separatory funnel. The aqueous layer was extracted with ethyl ether, and the organic layers were combined. The organic layer was washed 3 times with water and once with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, hexane (50 ml) was added to the obtained residue and the mixture was stirred. This slurry was filtered, and the obtained solid was washed with hexane, and dried under reduced pressure to give the title compound (12.23 g, 77%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. additionWater and ethyl ether were added to the filtrate
  3. customthe mixture was partitioned in a separatory funnel
  4. extractionThe aqueous layer was extracted with ethyl ether
  5. washThe organic layer was washed 3 times with water
  6. dry with materialonce with saturated brine, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure, hexane (50 ml)
  9. additionwas added to the obtained residue
  10. stirringthe mixture was stirred
  11. filtrationThis slurry was filtered
  12. washthe obtained solid was washed with hexane
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-0ac5b32abd1b45ebb7542bcd41bdd918
Source dataset
uspto-grants-2013_01
Patent number
US08343994B2

Reaction notes

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