Water → 2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)acetonitrile

HRID 1046025Notes

Reaction equation

HRID 1046025 reaction equation
[CH3:1][C:2]1([CH3:14])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[O:3]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].O.[C:24](#[N:26])[CH3:25]>>[CH3:1][C:2]1([CH3:14])[C:6]([CH3:7])([CH3:8])[O:5][B:4]([C:9]2[CH:13]=[N:12][N:11]([CH2:25][C:24]#[N:26])[CH:10]=2)[O:3]1

Participants

6

Reactant 5

HCID 962WaterHCID 5238Sodium IodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 674680952-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)acetonitrileYield 63%

Conditions

Temperature
70 °C

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.50 g, 2.58 mmol), sodium iodide (39 mg, 0.26 mmol) bromoacetonitrile (1.3 g, 10.8 mmol) and potassium carbonate (1.0 g, 7.8 mmol) in acetonitrile (10 mL) was heated at 70° C. overnight. Water was added and the solution was extracted with EtOAc (3×). The organic was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (10% to 100% EtOAc/hexane) to obtain 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)acetonitrile (0.38 g, 63% yield). MS (ESI) m/z: 234.1 (M+H+).

Workup

  1. extractionthe solution was extracted with EtOAc (3×)
  2. dry with materialThe organic was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (10% to 100% EtOAc/hexane)

Sources & evidence

ORD record
ord-d57990bef70843c89b2927b304d7b342
Source dataset
uspto-grants-2013_10
Patent number
US08569319B2

Reaction notes

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