Cesium fluoride → HCID 68891670, compound

HRID 1820997Notes

Reaction equation

HRID 1820997 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH:20]([CH3:22])[CH3:21])=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=3)[O:10][N:9]=2)=[C:4]([CH3:27])[CH:3]=1.[CH2:28]([Sn](CCCC)(CCCC)C=C)[CH2:29]CC.[F-].[Cs+]>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH:28]=[CH2:29])=[CH:3][C:4]=3[CH3:27])[N:12]=2)=[CH:14][C:15]=1[C:23]([F:26])([F:25])[F:24])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 81998TributylvinyltinHCID 68854028HCID 68854028, compound

Product 1

HCID 68891670HCID 68891670, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1.12 g (2.54 mmol) of 3-(4-bromo-2-methylphenyl)-5-(4-isopropoxy-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazole (EXAMPLE 12), 816 μL (2.79 mmol) of tributyl(vinyl)tin, and 848 mg (5.58 mmol) of cesium fluoride in 20 mL of 1,4-dioxane was added 32 mg (0.06 mmol) of bis(tri-tert-butylphosphine)palladium(0). After stirring at 100° C. for 2 h, the mixture was filtered through a cake of Celite and concentrated. Chromatography on Biotage 40M cartridge using 1:19 v/v EtOAc/hexanes as the eluant afforded 873 mg of the title compound.

Workup

  1. filtrationthe mixture was filtered through a cake of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-bc1b2ddd26964e4bad5b67eddcedb578
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

Loading…