Sodium Carbonate → HCID 67021267, compound

HRID 1660972Notes

Reaction equation

HRID 1660972 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]3[CH:17]=[CH:18][C:19](Br)=[CH:20][C:15]=3[N:14]=[CH:13]2)=[CH:8][CH:7]=1)[CH3:2].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+].B(O)O>C1(C)C=CC=CC=1.CCO.CCO.CCOC(C)=O.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]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([C:28]4[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=4)=[CH:20][C:15]=3[N:14]=[CH:13]2)=[CH:8][CH:7]=1)[CH3:2]

Participants

10

Reactant 4

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 201262(4-Methoxyphenyl)boronic acidHCID 67021635[4-(5-Bromo-benzoimidazol-1-yl)-phenyl]-acetic acid ethyl ester

Product 1

HCID 67021267HCID 67021267, compound

Reagents, catalysts & solvents 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21863594Toluene ethanolSolvent

Procedure

A mixture of [4-(5-bromo-benzoimidazol-1-yl)-phenyl]-acetic acid ethyl ester (0.300 g, 0.84 mmol), 4-methoxyphenylboronic acid (0.152 g, 1.00 mmol, 1.2 equiv), PdCl2(dppf) (18 mg, 0.025 mmol, 0.03 equiv), Na2CO3 (2 M solution in H2O, 1.7 mL, 3.34 mmol, 4 equiv) in toluene/EtOH (12 mL; 5:1, v/v) is stirred and refluxed for 2 h. After further addition of boronic acid (0.100 g, 0.66 mmol) in EtOH (1 mL), the reaction mixture is stirred and refluxed for 30 min, allowed to cool to rt, diluted with EtOAc and H2O, and filtered through a pad of Celite. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organic phase is washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Silica gel column chromatography purification (Hexane/EtOAc, 3:1) provides the title compound as a yellow solid: ES-MS: 387.1 [M+H]+; single peak at tR=4.27 min (System 1); Rf=0.24 (Hexane/EtOAc, 3:1).

Workup

  1. temperaturerefluxed for 2 h
  2. stirringthe reaction mixture is stirred
  3. temperaturerefluxed for 30 min
  4. filtrationfiltered through a pad of Celite
  5. customThe layers are separated
  6. extractionthe aqueous phase is extracted with EtOAc
  7. washThe combined organic phase is washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customSilica gel column chromatography purification (Hexane/EtOAc, 3:1)

Sources & evidence

ORD record
ord-219dc7064d8642329f035cb0067ebc95
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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