Potassium Carbonate → N-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanamide

HRID 2066429Notes

Reaction equation

HRID 2066429 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]([CH3:21])[C:17]([NH:19][CH3:20])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:20][NH:19][C:17](=[O:18])[CH: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)[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 148701962-bromo-N-methylpropanamide

Product 1

HCID 66995378N-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5.29 g, 27.3 mmol), 2-bromo-N-methylpropanamide (9.05 g, 54.5 mmol) and potassium carbonate (5.65 g, 40.9 mmol) in 136 ml acetone was refluxed for 68 hours. The white suspension was filtered through Celite with acetone washes; and the filtrate was concentrated and purified via silica gel chromatography (80 mm; 1 L 65% ethyl acetate/hexanes to 80% ethyl acetate/hexanes) to afford the title compound.

Workup

  1. temperaturewas refluxed for 68 hours
  2. filtrationThe white suspension was filtered through Celite with acetone washes
  3. concentrationand the filtrate was concentrated
  4. custompurified via silica gel chromatography (80 mm; 1 L 65% ethyl acetate/hexanes to 80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-4317900379c841c98fe195e5043087e6
Source dataset
uspto-grants-2012_10
Patent number
US08293738B2

Reaction notes

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