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Potassium Carbonate → 7-Hydroxy-2,4-diphenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

HRID 642281
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 642281
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10](Br)[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:15][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 866173544-Bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester

Produkt 1

HCID 684280397-Hydroxy-2,4-diphenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl esterAusbeute 36,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 4-bromo-7-hydroxy-2-phenyl-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (81 mg, 0.21 mmol), phenylboronic acid (34 mg, 0.28 mmol), tetrakis(triphenylphosphine)palladium(0)(25 mg, 0.02 mmol) and potassium carbonate (89 mg, 0.64 mmol) in dioxane (3 mL) and water (12 μL) was refluxed for 22 h before it was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane to give the title compound as a white solid (29 mg): 1H NMR (CDCl3, 200 MHz): δ=11.46 (s, 1H), 8.49 (m, 2H), 8.14 (m, 2H), 7.53 (m, 6H), 4.56 (q, J=7.0 Hz, 2H), 1.54 (t, J=7.0 Hz, 3H).

Aufarbeitung

  1. temperaturewas refluxed for 22 h before it
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b99074f3a1c348e6b0151de10752b432
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07696223B2

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