Cesium carbonate → 3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)butanenitrile

HRID 2090424Notes

Reaction equation

HRID 2090424 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.Br[CH:16]([CH3:20])[CH2:17][C:18]#[N:19].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[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]([CH:16]([CH3:20])[CH2:17][C:18]#[N:19])[CH:10]=2)[O:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 5492733-BromobutyronitrileHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 594023103-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)butanenitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (50 mg, 0.2 mmol), 3-bromobutanenitrile (46 mg, 0.31 mmol, TCI America, Cat. No. B 1452), and cesium carbonate (250 mg, 0.77 mmol) in acetonitrile (1 mL) was stirred at 90° C. for 3 hours. After cooling it was quenched with water, extracted with ethyl acetate. The extract was washed with water twice, brine once; dried over Na2SO4. After filtration the filtrate was concentrated to yield 60 mg product. It was directly used in the next step reaction without further purification.

Workup

  1. temperatureAfter cooling it
  2. customwas quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water twice
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration the filtrate
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-35e09b6c0aaa448c97897603bb4514c5
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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