Cesium carbonate → HCID 59773106, compound

HRID 2099546Notes

Reaction equation

HRID 2099546 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[CH:19]=[C:18](Br)[O:17][C:16]=2[CH3:21])=[O:14])=[CH:8][CH:7]=1)[CH3:2].CC1(C)C(C)(C)OB([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=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]>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[CH:19]=[C:18]([C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=3)[O:17][C:16]=2[CH3:21])=[O:14])=[CH:8][CH:7]=1)[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 59773105HCID 59773105, compound

Product 1

HCID 59773106HCID 59773106, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of {4-((5-bromo-2-methyl-furan-3-carbonyl)-amino]-phenyl}-acetic acid ethyl ester (3 g, 8.19 mmoles) (15), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (1.8 g, 8.19 mmoles), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (300 mg, 10%) and 2M aqueous cesium carbonate (15 ml, 15 mmoles) in N,N-dimethylformamide (35 ml) was heated in a microwave reactor at 100° C. for 15 minutes. The solvent was evaporated, and the residue was purified by flash chromatography (gradient elution with 100% cyclohexane to 100% ethyl acetate) to afford (4-{[5-(4-hydroxy-phenyl)-2-methyl-furan-3-carbonyl]-amino}-phenyl)-acetic acid ethyl ester (16) (1.9 g). LC/MS System A; Rt=3.54 mins, m/z (ES+)=380 (M+H for C22H21NO5).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography (gradient elution with 100% cyclohexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-a7537b1967ed44b589b75992234c098e
Source dataset
uspto-grants-2009_08
Patent number
US07569602B2

Reaction notes

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