Potassium Carbonate → HCID 67812377, compound

HRID 2279762Notes

Reaction equation

HRID 2279762 reaction equation
C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:12][CH:13]([CH3:23])[CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)=O.[CH3:24][C:25]1([CH3:37])[C:29]([CH3:31])([CH3:30])[O:28][B:27]([C:32]2[CH:33]=[N:34][NH:35][CH:36]=2)[O:26]1>CN(C=O)C>[CH2:16]([O:15][CH2:14][CH:13]([CH3:23])[CH2:12][N:35]1[CH:36]=[C:32]([B:27]2[O:26][C:25]([CH3:37])([CH3:24])[C:29]([CH3:31])([CH3:30])[O:28]2)[CH:33]=[N:34]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 86697714HCID 86697714, compound

Product 1

HCID 67812377HCID 67812377, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (0.855 g, 6.18 mmol) and 3-(benzyloxy)-2-methylpropyl methanesulfonate (Compound 18F, 1.46 g, 5.67 mmol) were added to a solution of 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (1.0 g, 5.2 mmol) in DMF (4 mL) and the mixture was allowed to stir at 80° C. overnight. The reaction was quenched with water (20 mL) and extracted with EtOAc (50 mL). The organic layer was washed with water (2×30 mL), washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified on a Teledyne ISCO Combiflash® Rf system using Heptane/EtOAc (70:30→30:70) as eluent to give the desired product as a light-yellow oil. 1H NMR (CDCl3, 400 MHz): δ=7.80 (s, 1H), 7.65 (s, 1H), 7.29-7.37 (m, 5H), 4.49 (s, 2H), 4.26, 4.04 (ABX, JAB=13.4 Hz, JAX=6.3 Hz, JBX=7.1 Hz, 2H), 3.32 (d, J=5.6 Hz, 2H), 2.41 (m, 1H), 1.33 (s, 12H), 0.95 (d, J=6.8 Hz, 3H).

Workup

  1. customThe reaction was quenched with water (20 mL)
  2. extractionextracted with EtOAc (50 mL)
  3. washThe organic layer was washed with water (2×30 mL)
  4. washwashed with brine (30 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified on a Teledyne ISCO Combiflash® Rf system

Sources & evidence

ORD record
ord-eddd4b7270484bf3837947e290128dba
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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