Cesium carbonate → HCID 59773096, compound

HRID 2099544Notes

Reaction equation

HRID 2099544 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[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][CH:16]=2)=[O:14])=[CH:8][CH:7]=1)[CH3:2].CC1(C)C(C)(C)OB([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=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:21])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C:15]2[CH:19]=[C:18]([C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=3)[O:17][CH:16]=2)=[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 59773104HCID 59773104, compound

Product 1

HCID 59773096HCID 59773096, compoundYield 38.2%

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-furan-3-carbonyl)-amino]-phenyl}-acetic acid ethyl ester (828 mg, 2.35 mmoles) (8), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (518 mg, 2.35 mmoles), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg) and 2M aqueous cesium carbonate (3.5 ml, 3.5 mmoles) in N,N-dimethylformamide (20 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 50% cyclohexane/50% ethyl acetate) to afford (4-{[5-(4-hydroxy-phenyl)-furan-3-carbonyl]-amino}-phenyl)-acetic acid ethyl ester (11) (328 mg). LC/MS System A; Rt=3.35 mins, m/z (ES+)=366 (M+H for C21H19NO5).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography (gradient elution with 100% cyclohexane to 50% cyclohexane/50% ethyl acetate)

Sources & evidence

ORD record
ord-3bf1421ff0be4434bc88f3a59003d3b3
Source dataset
uspto-grants-2009_08
Patent number
US07569602B2

Reaction notes

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