Sodium Bicarbonate → 2,2-Dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-1-ol

HRID 2279836Notes

Reaction equation

HRID 2279836 reaction equation
[CH3:1][C:2]([CH3:26])([CH2:18][O:19]C1CCCCO1)[CH2:3][N:4]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[N:5]1.CC1C=CC(S(O)(=O)=O)=CC=1.O.C([O-])(O)=O.[Na+]>CCO>[CH3:1][C:2]([CH3:26])([CH2:3][N:4]1[CH:8]=[C:7]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[N:5]1)[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 866977761-[2,2-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)propyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole2×

Product 1

HCID 678124422,2-Dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-1-olYield 57.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[2,2-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)propyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Compound 47C, 539 mg, 1.48 mmol) was dissolved in EtOH (2.64 mL) and p-TsOH.H2O (56.3 mg, 0.296 mmol) was added to the reaction mixture. The reaction was left to stir at rt for 16 hrs. Solid NaHCO3 (1.24 g, 14.8 mmol) was added to the reaction mixture and left to stir at rt for an additional 30 min. The reaction mixture was quenched with water and then extracted with EtOAc. The organic layer was washed with sat. NaHCO3 (1×), brine (2×), extracted, dried over sodium sulfate, filtered, concentrated in vacuo and purified using a Teledyne ISCO Combiflash® Rf system [0-30% Acetone/Heptanes] to afford 237 mg of the title compound (57%). MS (ESI): m/z=281.38 [M+H]+. UPLC: tR=1.12 min (UPLC-TOF: polar—2 min).

Workup

  1. waitThe reaction was left
  2. waitleft
  3. stirringto stir at rt for an additional 30 min
  4. customThe reaction mixture was quenched with water
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with sat. NaHCO3 (1×), brine (2×)
  7. extractionextracted
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. custompurified

Sources & evidence

ORD record
ord-c3ff203308734cb79352d93160d43f61
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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