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

HRID 2090409Notes

Reaction equation

HRID 2090409 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[CH2:16][CH2:17][C:18]#[N:19].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.C(OCC)(=O)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]([CH2:16][CH2:17][C:18]#[N:19])[CH:10]=2)[O:3]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 170203-BromopropionitrileHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 569657334-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-propanenitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (50 mg, 0.2 mmol), 3-bromopropionitrile (23 uL, 0.28 mmol, Aldrich, Cat. No. 109231) and cesium carbonate (250 mg, 0.77 mmol) in acetonitrile (1 mL) was stirred at 90° C. overnight. After cooling, it was diluted with ethyl acetate, washed with water twice and brine once, dried over Na2SO4. After filtration the filtrate was concentrated to yield 55 mg of the desired product.

Workup

  1. temperatureAfter cooling
  2. washwashed with water twice
  3. dry with materialbrine once, dried over Na2SO4
  4. filtrationAfter filtration the filtrate
  5. concentrationwas concentrated

Sources & evidence

ORD record
ord-645bd63a92a94e38a932e137a09c068e
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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