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

HRID 917298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917298
[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]

Komponenten

8

Edukt 4

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 132827592-Bromo-4-trifluoromethyl-thiazole-5-carboxylic acid ethyl ester

Produkt 1

HCID 1483699Ethyl 2-phenyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxylateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c71c4c60496a41b38418b116bdafcbe5
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273866B2

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