HCID 90000661, compound → HCID 89995762, compound

HRID 523101Notes

Reaction equation

HRID 523101 reaction equation
[CH3:1][C:2]1([CH3:19])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][N:12]([CH:14]([CH3:18])[C:15](=[O:17])[CH3:16])[CH:13]=2)[O:3]1.[CH3:20][Mg+].[Br-]>C1COCC1.[Cl-].[Na+].O>[CH3:16][C:15]([OH:17])([CH:14]([N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:19])([CH3:1])[O:3]2)[CH:10]=[N:11]1)[CH3:18])[CH3:20]

Participants

5

Reactant 2

HCID 90000661HCID 90000661, compoundHCID 178418689HCID 178418689, compound2×

Product 1

HCID 89995762HCID 89995762, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)butan-2-one (Preparation 133, in THF (6 mL) at 0° C. was added MeMgBr (3M, 0.24 mL, 0.71 mmol). After stirring for 3 hours, another portion of MeMgBr was added. The solution was stirred at room temperature for 16 hours. The reaction was diluted with brine and extracted with EtOAc. The combined organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo to afford the title compound as a yellow oil (99 mg, 70%).

Workup

  1. stirringThe solution was stirred at room temperature for 16 hours
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe38bb9bcba6499b840dc959363ed104
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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