Dimethylformamide → 3-((4-Iodo-1H-pyrazol-1-yl)methyl)-5-methylisoxazole

HRID 2205869Notes

Reaction equation

HRID 2205869 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.Br[CH2:8][C:9]1[CH:13]=[C:12]([CH3:14])[O:11][N:10]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(OCC)(=O)C>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2[CH:13]=[C:12]([CH3:14])[O:11][N:10]=2)[CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 770224-IodopyrazoleHCID 27763043-(Bromomethyl)-5-methylisoxazole

Product 1

HCID 644297653-((4-Iodo-1H-pyrazol-1-yl)methyl)-5-methylisoxazoleYield 56.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Iodo-1H-pyrazole (0.826 g, 4.26 mmol) (1), 3-(bromomethyl)-5-methylisoxazole (0.75 g, 4.26 mmol) and potassium carbonate (1.18 g, 8.52 mmol) were added to dry DMF (8 ml) and stirred at room temperature for 16 h. The reaction was diluted with ethyl acetate (20 ml) and washed with water, brine and dried. The organic solution was concentrated in vacuo and the residue purified by flash silica chromatography (20% ethyl acetate in hexane). The pure fractions provided the title compound as a white powder (0.7 g, 56.8%). 1H-NMR (500 MHz, CDCl3) 2.4 (s, 3H), 5.33 (s, 2H), 5.92 (s, 1H), 7.51 (s, 1H), 7.55 (s, 1H).

Workup

  1. washwashed with water, brine
  2. customdried
  3. concentrationThe organic solution was concentrated in vacuo
  4. customthe residue purified by flash silica chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-dddfd510e75f4bc4b236c5ead7a13f93
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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