Water → HCID 69515985, compound

HRID 1351091Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:36]=[CH:35][CH:34]=[CH:33][C:10]=1[CH2:11][C:12]1[C:13]([O:21][C@@H:22]2[O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]([OH:26])[C@H:23]2[OH:24])=[N:14][NH:15][C:16]=1[C:17]([F:20])([F:19])[F:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:38][CH2:39][O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:36]=[CH:35][CH:34]=[CH:33][C:10]=1[CH2:11][C:12]1[C:13]([O:21][C@@H:22]2[O:30][C@H:29]([CH2:31][OH:32])[C@@H:27]([OH:28])[C@H:25]([OH:26])[C@H:23]2[OH:24])=[N:14][N:15]([CH2:38][CH2:39][O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:16]=1[C:17]([F:18])([F:20])[F:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(2-benzyloxybenzyl)-3-(β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole (300 mg) in N,N-dimethylformamide (3 mL) were added (2-bromoethoxymethyl)benzene (379 mg) and cesium carbonate (957 mg), and the mixture was stirred at 80° C. for 1.5 hours. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=20/1-10/1) to give the title compound (154 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was removed under reduced pressure
customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=20/1-10/1)

Sources & evidence

ORD record: ord-389b57ce79ad4fe0a97d3abb231a79fe
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217697B2

Reaction notes

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