Cesium carbonate → N-[2-(9-Oxo-9H-xanthen-3-yl)-phenyl]-acetamide

HRID 1987934Notes

Reaction equation

HRID 1987934 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[C:17]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O)(=[O:19])[CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+].O1CCOCC1>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(O)C>[O:16]=[C:6]1[C:5]2[CH:4]=[CH:3][C:2]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[NH:20][C:17](=[O:19])[CH3:18])=[CH:15][C:14]=2[O:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 2316083-Bromo-9H-xanthen-9-oneHCID 27377892-Acetamidophenylboronic acid

Product 1

HCID 57725319N-[2-(9-Oxo-9H-xanthen-3-yl)-phenyl]-acetamide

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolvent

Procedure

3-Bromo-xanthen-9-one (0.25 g, 0.9 mmol), 2-acetamidophenylboronic acid (0.99 mmol), 1,1′-bis-(diphenylphosphino)ferrocene-palladium (II) dichloride (33 mg, 0.045 mmol), cesium carbonate (0.59 g, 1.8 mmol), dioxane (4 mL), and ethanol (2 mL) were microwaved in a 5-mL reaction vessel at 100° C. for 5 min. The reaction was filtered and concentrated. The residue was purified by reverse phase chromatography to afford N-[2-(9-Oxo-9H-xanthen-3-yl)-phenyl]-acetamide.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated
  3. customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-c3dd7df7be094a058fcd97dbe720d316
Source dataset
uspto-grants-2009_06
Patent number
US07553850B2

Reaction notes

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