Sodium hydride → HCID 67207894, compound

HRID 1253466Notes

Reaction equation

HRID 1253466 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.FC(F)(F)S(O[CH2:23][CH:24]([F:34])[CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])(=O)=O>CN(C=O)C.C(OCC)C>[Si:27]([O:26][CH2:25][CH:24]([F:34])[CH2:23][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)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 57927181HCID 57927181, compound

Product 1

HCID 67207894HCID 67207894, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Procedure

NaH (0.247 g, 6.17 mmol) was suspended in 10 mL of DMF. 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.958 g, 4.94 mmol) was added in 5 mL of DMF dropwise via syringe and the mixture was stirred at room temperature for 30 minutes. Then 3-{[tert-butyl(dimethyl)silyl]oxy}-2-fluoropropyl trifluoromethanesulfonate (1.40 g, 4.11 mmol) was added in 5 mL of DMF dropwise via syringe. After 20 minutes, the reaction mixture was diluted in diethyl ether, washed with water (3×50 mL) and brine then dried over magnesium sulfate, filtered and concentrated to afford 1-(3-{[tert-butyl(dimethyl)silyl]oxy}-2-fluoropropyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole.

Workup

  1. waitAfter 20 minutes
  2. washwashed with water (3×50 mL) and brine
  3. dry with materialthen dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-058e8dd952c3404f9a113c799e6c1764
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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