Potassium Iodide → HCID 22261191, compound

HRID 1609937Notes

Reaction equation

HRID 1609937 reaction equation
C([O:3][C:4](=[O:31])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])C.[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[C:41]([O-:44])([O-])=O.[K+].[K+].[I-].[K+]>C1(OC)C=CC=CC=1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[C:20]([C:24]1[CH:29]=[CH:28][C:41]([O:44][C:27]2[CH:26]=[CH:25][C:24]([C:20]3[O:21][C:22]([CH3:23])=[C:18]([CH2:17][CH2:16][O:15][C:12]4[CH:11]=[CH:10][C:9]([O:8][C:5]([CH3:7])([CH3:6])[C:4]([OH:3])=[O:31])=[CH:14][CH:13]=4)[N:19]=3)=[CH:29][CH:28]=2)=[CH:26][CH:25]=1)(=[O:21])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 110273422-(4-{2-[2-(4-Bromophenyl)-5-methyloxazol-4-yl]ethoxy}phenoxy)-2-methylpropionic acid ethyl ester

Product 1

HCID 22261191HCID 22261191, compoundYield 51.5%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 7519AnisoleSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(4-{2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester (0.20 g, 0.410 mmol), phenyl boronic acid (0.055 g, 0.451 mmol), powdered K2CO3 (0.169 g, 1.22 mmol), potassium iodide (0.20 g, 1.20 mmol), 1,1′-bis(diphenylphosphino) ferrocene (0.023 g, 0.0414 mmol) and palladium (II) chloride (0.007 g, 0.0395 mmol) in anisole (4 mL) and then carbon monoxide was bubbled through the reaction mixture to saturate the mixture. The reaction was then heated at 80° C. in an oil bath under a carbon monoxide balloon for 2 h. The reaction was cooled, diluted with Et2O, and extracted with water and brine. The organic layer was dried (MgSO4) and the solvent removed in vacuo to give an oil that passed over a plug of silica gel to remove most of the anisole (98:2 ratio CH2Cl2:MeOH). The resultant oil was dissolved in EtOH (8 mL) and treated with 5 N NaOH (0.1 ml) at reflux for 1 h. The reaction mixture was cooled, acidified with 1 N HCl (1 mL) and the reaction mixture extracted with EtOAc and water to give 0.061 g of crude 2-[4-(2-{2-[4-(4-benzoyl-phenoxy)-phenyl]-5-methyl-oxazol-4-yl}-ethoxy)-phenoxy]-2-methyl-propionic acid that was purified by LCMS to afford 0.017 g of 2-[4-(2-{2-[4-(4-benzoyl-phenoxy)-phenyl]-5-methyl-oxazol-4-yl}-ethoxy)-phenoxy]-2-methyl-propionic acid.

Workup

  1. customcarbon monoxide was bubbled through the reaction mixture
  2. concentrationto saturate the mixture
  3. temperatureThe reaction was cooled
  4. additiondiluted with Et2O
  5. extractionextracted with water and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customto give an oil that
  9. customto remove most of the anisole (98:2 ratio CH2Cl2:MeOH)
  10. dissolutionThe resultant oil was dissolved in EtOH (8 mL)
  11. additiontreated with 5 N NaOH (0.1 ml)
  12. temperatureat reflux for 1 h
  13. temperatureThe reaction mixture was cooled
  14. extractionthe reaction mixture extracted with EtOAc and water

Sources & evidence

ORD record
ord-028ec7a94140470088ec64d275d9ce9c
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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