1,2-Dimethoxyethane → HCID 58365686, compound

HRID 2037191Notes

Reaction equation

HRID 2037191 reaction equation
[CH3:1][CH:2]([CH3:27])[C:3]([C:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[N:8]([C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=2)[C:7](=[O:25])[C:6]=1[OH:26])=[O:4].[S:28]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].COCCOC>O>[CH3:1][CH:2]([CH3:27])[C:3]([C:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[N:8]([C:18]2[CH:23]=[CH:22][C:21]([C:30]3[CH:31]=[CH:32][S:28][CH:29]=3)=[CH:20][CH:19]=2)[C:7](=[O:25])[C:6]=1[OH:26])=[O:4]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 581760Thiophene-3-boronic acidHCID 58365489HCID 58365489, compound

Product 1

HCID 58365686HCID 58365686, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

After a mixture of (−)-4-(2-methylpropionyl)-3-hydroxy-1-(4-bromophenyl)-5-(2-methoxyphenyl)-1,5-dihydropyrrole-2-one (0.10 g, 0.23 mmol), 3-thiophene-boronic acid (0.045 g, 0.35 mmol), tripotassium phosphate (0.148 g, 0.7 mmol), 1,2-dimethoxyethane (3 mL) and water (3 mL) was placed in a flask under nitrogen, 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.019 g, 0.023 mmol) was added to the mixture, and the resulting mixture was stirred at reflux for 3 hours. To the reaction mixture was added water (50 mL), and the resulting mixture was extracted with dichloromethane (50 mL). The extract was washed with brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resulting residue was purified on a silica gel column chromatography (methanol/chloroform). The resulting compound was triturated with ethyl acetate/n-hexane to give (−)-4-(2-methylpropionyl)-3-hydroxy-1-(4-thiophene-3-ylphenyl)-5-(2-methoxyphenyl)-1,5-dihydropyrrole-2-one (0.029 g, yield: 29%) as pale brown powder.

Workup

  1. customwas placed in a flask under nitrogen
  2. addition1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.019 g, 0.023 mmol) was added to the mixture
  3. temperatureat reflux for 3 hours
  4. extractionthe resulting mixture was extracted with dichloromethane (50 mL)
  5. washThe extract was washed with brine (50 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified on a silica gel column chromatography (methanol/chloroform)
  9. customThe resulting compound was triturated with ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-1e0898f1c43147af88d861cb23b64769
Source dataset
uspto-grants-2013_11
Patent number
US08575197B2

Reaction notes

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