Sodium Iodide → 1-(cyclopropylmethyl)-3-(beta-D-glucopyranosyloxy)-5-methyl-4-[(4methylthiophenyl)methyl]-1H-pyrazole

HRID 457521

Reaction equation

HRID 457521 reaction equation
[C@@H:1]1([O:12][C:13]2[C:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=3)=[C:16]([CH3:27])[NH:15][N:14]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:35][CH:36]1[CH2:38][CH2:37]1.[I-].[Na+]>CN(C)C=O.O>[CH:36]1([CH2:35][N:15]2[C:16]([CH3:27])=[C:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=3)[C:13]([O:12][C@@H:1]3[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]3[OH:3])=[N:14]2)[CH2:38][CH2:37]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 99526103-(beta-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole

Product 1

HCID 235455141-(cyclopropylmethyl)-3-(beta-D-glucopyranosyloxy)-5-methyl-4-[(4methylthiophenyl)methyl]-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole (0.081 g) in N,N-dimethylformamide (1 mL) were added cesium carbonate (0.40 g), bromomethylcyclopropane (0.099 mL) and a catalytic amount of sodium iodide, and the mixture was stirred at room temperature for 7 days. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-8/1) to give 1-(cyclopropylmethyl)-3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole (0.041 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-8/1)

Sources & evidence

ORD record
ord-40523d8aeb5c4977bc68c1d0bd3362d3
Source dataset
uspto-grants-2007_03
Patent number
US07189702B2

Linked notes

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