Sodium hydride → 1-(2,2-difluoroethyl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

HRID 1480841Notes

Reaction equation

HRID 1480841 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:16])[C:8]([CH3:10])([CH3:9])[O:7][B:6]([C:11]2[CH:12]=[N:13][NH:14][CH:15]=2)[O:5]1.[F:17][CH:18]([F:21])[CH2:19]I>CN(C=O)C.[Cl-].[Na+].O>[F:17][CH:18]([F:21])[CH2:19][N:14]1[CH:15]=[C:11]([B:6]2[O:7][C:8]([CH3:9])([CH3:10])[C:4]([CH3:16])([CH3:3])[O:5]2)[CH:12]=[N:13]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 38335651,1-Difluoro-2-iodoethane

Product 1

HCID 899961951-(2,2-difluoroethyl)-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

NaH (60%, 128 mg) was added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (313 mg, 1.61 mmol) in DMF (4 mL). After stirring for 15 minutes, 1,1-difluoro-2-iodoethane (372 mg, 1.94 mmol) in DMF (1 mL) was added. The resulting solution was stirred at 80° C. under microwave irradiation for 60 minutes. The reaction mixture was diluted with brine and extracted with EtOAc. The combined organic layers were washed with water, dried with Na2SO4, and concentrated in vacuo to afford the title compound as a yellow oil that was used directly in the next step (210 mg, 50%).

Workup

  1. stirringThe resulting solution was stirred at 80° C. under microwave irradiation for 60 minutes
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd6bc531f5074247a8edcd904b09570d
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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