(4-Methoxyphenyl)boronic acid → Ethyl 2-(4-methoxyphenyl)thiazole-4-carboxylate

HRID 1500260Notes

Reaction equation

HRID 1500260 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](Br)[S:9][CH:10]=1)=[O:5])[CH3:2].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)[S:9][CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 201262(4-Methoxyphenyl)boronic acidHCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 22031701Potassium phosphate, tribasic, monohydrate

Product 1

HCID 10400532Ethyl 2-(4-methoxyphenyl)thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

2-Bromo-thiazole-4-carboxylic acid ethyl ester (1.00 mmol, 236 mg), 4-methoxyphenylboronic acid (1.50 mmol, 228 mg), Pd2(DBA)3 (0.020 mmol, 18 mg), S-Phos (0.060 mmol, 25 mg) and potassium phosphate tribasic monohydrate (1.5 mmol, 0.35 g) were loaded into a Schlenk tube containing a stir bar. The Schlenk tube was capped with a rubber septum, evacuated and refilled with nitrogen. Toluene (2 mL) was added through the septum via a syringe and the Schlenk tube was sealed with a Teflon screw cap under a flow of nitrogen, and put into an oil bath at 100° C. The reaction was allowed to stir at 100° C. for 15 hours, then the reaction mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated in vacuo and the resultant crude residue was purified using column chromatography on silica gel (eluent: Hexane/EtOAc (4:1)) to provide 2-(4-Methoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester as a yellowish solid.

Workup

  1. additioncontaining a stir bar
  2. customThe Schlenk tube was capped with a rubber septum
  3. customevacuated
  4. additionrefilled with nitrogen
  5. additionToluene (2 mL) was added through the septum via a syringe
  6. customthe Schlenk tube was sealed with a Teflon
  7. customscrew cap under a flow of nitrogen
  8. customput into an oil bath at 100° C
  9. temperaturethe reaction mixture was cooled to room temperature
  10. filtrationfiltered through celite
  11. concentrationThe filtrate was concentrated in vacuo
  12. customthe resultant crude residue was purified

Sources & evidence

ORD record
ord-4d36a83c1e664bcbb7c3d57263cbbcc8
Source dataset
uspto-grants-2015_12
Patent number
US09206142B2

Reaction notes

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