Cesium fluoride → 4-{[4-(4-fluoro-phenyl)phenyl]methyl}-5-methyl-3-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-1H-pyrazole

HRID 7375

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10]([O:15][C@@H:16]3[O:33][C@H:32]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[C@@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]3[O:18][C:19](=[O:21])[CH3:20])=[N:11][NH:12][C:13]=2[CH3:14])=[CH:4][CH:3]=1.[F:39][C:40]1[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1.[F-].[Cs+]>COCCOC.C(O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:39][C:40]1[CH:45]=[CH:44][C:43]([C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]3[C:10]([O:15][C@@H:16]4[O:33][C@H:32]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:34]([O:35][C:36](=[O:38])[CH3:37])[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:17]4[O:18][C:19](=[O:21])[CH3:20])=[N:11][NH:12][C:13]=3[CH3:14])=[CH:6][CH:7]=2)=[CH:42][CH:41]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 4-[(4-bromophenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.099 g), 4-fluorophenylboronic acid (0.046 g), cesium fluoride (0.050 g) and tetrakis(triphenylphosphine)palladium(0) (0.0038 g) in 1,2-dimethoxyethane (1.3 mL), ethanol (0.3 mL) and water (0.3 mL) was stirred at 85° C. for 18 hours. The reaction mixture was purified by column chromatography on silica gel (eluent: hexane/ethylacetate=1/1-1/2-1/5) to give 4-{[4-(4-fluorophenyl)phenyl]methyl}-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.061 g).

Workup

customThe reaction mixture was purified by column chromatography on silica gel (eluent: hexane/ethylacetate=1/1-1/2-1/5)

Sources & evidence

ORD record: ord-d817accfc9194d7d8c056a712cc00b72
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087579B2

Linked notes

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