Cesium carbonate → HCID 59773103, compound

HRID 2099543Notes

Reaction equation

HRID 2099543 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].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.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:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[O:17][CH:16]=2)=[O:14])=[CH:8][CH:7]=1)[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 59773104HCID 59773104, compound

Product 1

HCID 59773103HCID 59773103, compoundYield 26.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Procedure

A solution of {4-[(5-bromo-furan-3-carbonyl)-amino]-phenyl}-acetic acid ethyl ester (8) (200 mg, 0.57 mmoles), phenyl boronic acid (69.2 mg, 0.57 mmoles), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg, 0.06 mmoles) and 2M aqueous cesium carbonate (1.2 ml, 2.4 mmoles) in toluene (20 ml) was refluxed for 16 hours. The solvent was evaporated, the residue diluted with water (20 ml) and then extracted with ethyl acetate (3×20 ml). The combined organic layers were concentrated in vacuo. The residue was was purified by flash chromatography (gradient elution with 90% cyclohexane/10% ethyl acetate to 50% cyclohexane/50% ethyl acetate) to afford {4-[(5-phenyl-furan-3-carbonyl)-amino]-phenyl}-acetic acid ethyl ester (9) (53 mg). LC/MS System A; Rt=3.84 mins, m/z (ES+)=(M+H for C21H19NO4).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue diluted with water (20 ml)
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. concentrationThe combined organic layers were concentrated in vacuo
  5. customThe residue was was purified by flash chromatography (gradient elution with 90% cyclohexane/10% ethyl acetate to 50% cyclohexane/50% ethyl acetate)

Sources & evidence

ORD record
ord-fa27fc5eb88242f784c8a7821bcca37b
Source dataset
uspto-grants-2009_08
Patent number
US07569602B2

Reaction notes

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