Cesium carbonate → 2-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-ol

HRID 2047073Notes

Reaction equation

HRID 2047073 reaction equation
[NH:1]1[CH:5]=[C:4]([B:6]2[O:14][C:11]([CH3:13])([CH3:12])[C:8]([CH3:10])([CH3:9])[O:7]2)[CH:3]=[N:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:21][C:22]1([O:25][CH2:24]1)[CH3:23]>CN(C=O)C>[CH3:21][C:22]([OH:25])([CH3:24])[CH2:23][N:2]1[CH:3]=[C:4]([B:6]2[O:7][C:8]([CH3:9])([CH3:10])[C:11]([CH3:13])([CH3:12])[O:14]2)[CH:5]=[N:1]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11208Isobutylene oxideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 582041312-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a 20 mL pressure vial was charged pyrazole-4-boronic acid pinacol ester (5.15 mmol, 1.00 g), DMF (10 mL), and Cs2CO3 (5.67 mmol, 1.85 g). To this suspension was added isobutylene oxide (15.45 mmol, 1.38 mL). The vial was flushed with argon and sealed. The reaction was stirred 18 hours at 80° C. After 18 hours, the reaction was filtered through celite and the solvent removed in vacuo. This residue was pumped dry under high vacuum and then purified via flash chromatography to yield the title compound.

Workup

  1. customThe vial was flushed with argon
  2. customsealed
  3. waitAfter 18 hours
  4. filtrationthe reaction was filtered through celite
  5. customthe solvent removed in vacuo
  6. customThis residue was pumped dry under high vacuum
  7. custompurified via flash chromatography

Sources & evidence

ORD record
ord-1b6cebaebdeb4351b1a29c143bdd9c11
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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