Potassium Carbonate → HCID 89650960, Verbindung

HRID 2174689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174689
CC1S[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:25]([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O.O>[CH:13]1([C:14]2[N:6]=[C:5]([C:7]([O:9][CH3:25])=[O:8])[C:4]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:10][CH:15]=2)[CH2:12][CH2:11]1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 9435352-methyl-5-phenyl-1,3-thiazole-4-carboxylic Acid

Produkt 1

HCID 89650960HCID 89650960, VerbindungAusbeute 74,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a suspension of 6-Cyclopropyl-3-iodo-pyridine-2-carboxylic acid methyl ester (D85, 200 mg, 0.66 mmol), phenyl boronic acid (80.5 mg, 0.66 mmol) and Pd tetrakistriphenylphospine (76.3 mg; 0.066 mmol) in dry Toluene (3 ml) was added K2CO3 (1M acq solution, 0.66 ml, 0.66 mmol). The mixture was heated in microwave oven for 25 min at 120° C. The reaction mixture was diluted with AcOEt (10 mL) and water (10 mL). The organic layer was separated, washed with brine, dried over Na2SO4 and filtrated. The solvent was evaporated under reduced pressure; the crude mixture was purified on silica gel (Cyclohexane to Cyclohexane/AcOEt 9:1) to obtain 125 mg of the title compound as white solid.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltrated
  5. customThe solvent was evaporated under reduced pressure
  6. customthe crude mixture was purified on silica gel (Cyclohexane to Cyclohexane/AcOEt 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-2ee247eac92e41d4842ace4bf2569b27
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062033B2

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