Water → Ethyl 2-(4-nitrophenyl)-1,3-thiazole-5-carboxylate

HRID 1425032Notes

Reaction equation

O.[N+:2]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([O-:4])=[O:3].Br[C:15]1[S:16][C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][N:19]=1.C(=O)(O)[O-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O1CCOCC1>[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C:15]2[S:16][C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][N:19]=2)=[CH:7][CH:6]=1)([O-:4])=[O:3]

Participants

Conditions

Temperature: 100 °C

Procedure

Water (5 mL) and 1,4-dioxane (5 mL) were added to 4-nitrophenylboronic acid (667 mg, 4 mmol), ethyl 2-bromo-1,3-thiazole-5-carboxylate (448 μL, 4 mmol), sodium bicarbonate (1.01 g, 12 mmol) and tetrakis(triphenylphosphine)palladium (462 mg, 0.4 mmol), and the mixture was stirred in a nitrogen atmosphere at 100° C. for 1.5 hours. Ethyl acetate was added to the reaction solution, and the organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=10/1, 4/1, 2/1) to obtain 0.6 g of the title compound as a colorless solid (54%).

Workup

washthe organic layer was washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentration under reduced pressure
customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=10/1, 4/1, 2/1)

Sources & evidence

ORD record: ord-7c3f11bf0f204cd684a4e093e10407b7
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927588B2

Reaction notes

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