Potassium Fluoride → (5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-fluoromethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

HRID 459020

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH2:20]Br)[N:17]=[N:16]3)[O:11][C:10]2=[O:22])[CH:5]=[CH:6][C:7]=1[I:8].[F-].[K+].[F:25][B-](F)(F)F.C([N+]1C=CN(C)C=1)CCC>C(#N)C.O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH2:20][F:25])[N:17]=[N:16]3)[O:11][C:10]2=[O:22])[CH:5]=[CH:6][C:7]=1[I:8]

Participants

Conditions

Temperature: 90 °C

Procedure

(5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-bromomethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one (Intermediate 17, 6.94 g, 14.4 mmol) was dissolved/suspended in acetonitrile (250 mL) and water (1.5 mL). Potassium fluoride (4.19 g, 72.1 mmol) was added, followed by addition of 1-butyl-3-methylimidazolium tetrafluoroborate (18.4 mL) and the solution was heated to 90° C. over night. It was diluted with ethyl acetate, washed with water and dried over magnesium sulfate. Chromatography on silica gel with ethyl acetate gave 2.7 g (45%) of the title compound as an off-white solid.

Workup

washwashed with water
dry with materialdried over magnesium sulfate

Sources & evidence

ORD record: ord-59bc19a313014abd889ce5c5dc1b0897
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192974B2

Linked notes

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