Cesium carbonate → HCID 66772508, compound

HRID 1645262Notes

Reaction equation

HRID 1645262 reaction equation
Br[C:2]1[O:6][C:5]([CH:7]=[C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:17])=[C:4]([CH3:18])[CH:3]=1.[CH3:19][O:20][C:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].C([O-])([O-])=O.[Cs+].[Cs+]>O.O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:18][C:4]1[CH:3]=[C:2]([C:27]2[CH:28]=[C:23]([CH:24]=[CH:25][CH:26]=2)[C:21]([O:20][CH3:19])=[O:22])[O:6][C:5]=1[CH:7]=[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:17]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 66772224HCID 66772224, compound

Product 1

HCID 66772508HCID 66772508, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of 3-((5-bromo-3-methylfuran-2-yl)methylene)indolin-2-one (125 mg, 0.41 mmol), 3-(methoxycarbonyl)phenylboronic acid (115 mg, 0.64 mmol), Cs2CO3 (270 mg, 0.83 mmol) and PdCl2(dppf) (16 mg, 0.02 mmol) in H2O/dioxane (5%, 5 mL) was heated at reflux for 1 h. The reaction mixture was diluted with H2O (150 mL) and extracted with EtOAc (3×100 mL). The organic layer was washed with brine (100 mL) and dried over Na2SO4 and concentrated to yield the desired methyl 3-(4-methyl-5-((2-oxoindolin-3-ylidene)methyl)furan-2-yl)benzoate. LCMS (ES): m/z 360 [M+1]+.

Workup

  1. temperatureat reflux for 1 h
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe organic layer was washed with brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1d8e39f47bab4115bb0dcbf3e6801913
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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