Dimethyl Sulfoxide → Methyl 4'-methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylate

HRID 1845267Notes

Reaction equation

HRID 1845267 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:26]1[S:27][CH:28]=[CH:29][N:30]=1.CS(C)=O>CCOC(C)=O>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[CH:7]=[C:2]([O:1][C:26]3[S:27][CH:28]=[CH:29][N:30]=3)[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 58187967Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 58187983Methyl 4'-methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of methyl 5-hydroxy-4′-methylbiphenyl-3-carboxylate (100 mg, 0.41 mmol), potassium carbonate (114 mg, 0.83 mmol), 2-bromothiazole (0.38 mL, 4.2 mmol), and dimethyl sulfoxide (2.5 mL) was stirred at 135° C. overnight. After cooling, the mixture was diluted with EtOAc and washed with aq. NaHCO3 (sat.), dried over anhydrous MgSO4, and concentrated. The residue was purified by flash chromatography (0-20% EtOAc/hexane) to afford the title compound.

Workup

  1. temperatureAfter cooling
  2. washwashed with aq. NaHCO3 (sat.)
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (0-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-ac8b1129f3c34aacb66939bd96334b84
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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