Phenylboronic Acid → Ethyl 2-phenyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

HRID 917298Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9](Br)=[N:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[F-].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)C>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of thiazole III (2.0 g, 6.6 mmol) and the phenyl boronic acid (9.9 mmol) in THF (10 mL) was added potassium fluoride (1.15 g, 19.8 mmol), palladium (II) acetate (74 mg, 0.33 mmol), and 2-(di-t-butylphosphino)biphenyl (197 mg, 0.66 mmol). This mixture was stirred at 25° C. for 24 h. Diethyl ether (100 mL) was then added and the mixture was washed with 1 N aqueous NaOH (2×50 mL), saturated aqueous NaCl (1×50 mL), dried over MgSO4 and concentrated in vacuo to give an off-white solid. Purification by flash chromatography (silica, 0-2.5% ethyl acetate/hexane) gave the product, generally in 60-90% yield.

Workup

washthe mixture was washed with 1 N aqueous NaOH (2×50 mL), saturated aqueous NaCl (1×50 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto give an off-white solid
customPurification by flash chromatography (silica, 0-2.5% ethyl acetate/hexane)
customgave the product

Sources & evidence

ORD record: ord-c71c4c60496a41b38418b116bdafcbe5
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273866B2

Reaction notes

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