Cesium carbonate → HCID 86707274, compound

HRID 576066Notes

Reaction equation

HRID 576066 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[CH:10]1([CH2:15]/[CH:16]=[CH:17]/B2OC(C)(C)C(C)(C)O2)[CH2:14][CH2:13][CH2:12][CH2:11]1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[CH:10]1([CH2:15]/[CH:16]=[CH:17]/[C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 1230504-Bromo-2-fluoroanilineHCID 521585Tris(furan-2-yl)phosphaneHCID 162181952-[(1E)-3-Cyclopentylprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 86707274HCID 86707274, compoundYield 91.8%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

1,4-Dioxane (5 mL) and water (1.2 mL) were added to 4-bromo-2-fluoroaniline (285 mg, 1.50 mmol), trans-3-(cyclopentyl)propenylboronic acid pinacol ester (425 mg, 1.80 mmol), tris(dibenzylidene acetone)dipalladium (137 mg, 0.15 mmol), tri-2-furylphosphine (210 mg, 0.90 mmol) and cesium carbonate (976 mg, 3.00 mmol). The mixture was heated to an external temperature of 100° C. and stirred for 6 hr, under a nitrogen atmosphere. After cooling, the mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried over anhydrous magnesium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane only→hexane:ethyl acetate=9:1) to afford the title compound as a pale yellow oil (302 mg).

Workup

  1. temperatureAfter cooling
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationthe desiccant was filtered off
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane only→hexane

Sources & evidence

ORD record
ord-97911015bf3c4f2e969f69206e1790ad
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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