Cesium carbonate → N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-Pyrazole-1-acetamide

HRID 1925124Notes

Reaction equation

HRID 1925124 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.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:22][C:23]([N:25]([CH3:27])[CH3:26])=[O:24]>CN(C=O)C.O>[CH3:26][N:25]([CH3:27])[C:23](=[O:24])[CH2:22][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 758862-chloro-N,N-dimethylacetamideHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 57891415N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-Pyrazole-1-acetamideYield 113.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.8 g, 4.1 mmol), cesium carbonate (2.0 g, 6.2 mmol), and 2-chloro-N,N-dimethylacetamide (0.47 mL, 4.5 mmol) in DMF (14 mL) was heated in a microwave at 90° C. for 1 hr. The crude reaction mixtures were then diluted with water (300 mL) and extracted with ethyl acetate (3×50 mL). Product was purified by silica gel column using DCM/EtOAc/MeOH (8/1.5/0.5) as eluent to provide N,N-dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)acetamide (1.3 g) as a light yellow oil. ESI-MS:m/z 280.3 (M+H)+.

Workup

  1. customThe crude reaction mixtures
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. customProduct was purified by silica gel column

Sources & evidence

ORD record
ord-9443a87e972b455baa79bb652264a5e3
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

Loading…