Cesium carbonate → 1H-Pyrazole, 1-[2-(2-methoxyethoxy)ethyl]-4(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

HRID 69256Notes

Reaction equation

HRID 69256 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][O:18][CH2:19][CH2:20][O:21][CH3:22].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH3:22][O:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][N:12]1[CH:13]=[C:9]([B:4]2[O:5][C:6]([CH3:7])([CH3:8])[C:2]([CH3:14])([CH3:1])[O:3]2)[CH:10]=[N:11]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1235321-Bromo-3,6-dioxaheptaneHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 686319071H-Pyrazole, 1-[2-(2-methoxyethoxy)ethyl]-4(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (500 mg, 2.58 mmol), 1-(2-bromo-ethoxy)-2-methoxy-ethane (566 mg, 3.09 mmol) and Cs2CO3 (840 mg, 2.58 mmol) in DMF (5 mL) was stirred at 95° C. for 18 h. The mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated to afford the title compound as an oil. (MH+=297.1, 1H-NMR in CDCl3: 7.77 (m, 1 or 2H) 4.31 (t, 2H); 3.85 (t, 2H); 3.54 (m, 2H); 3.48 (m, 2H); 3.35 (s, 3H); 1.31 (s, 12H)).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-568738618d114d64a21bc1af6cf901a1
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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