Sodium Carbonate → 5-(6-Methoxy-benzothiazol-2-yl)-thiophene-2-carboxylic acid

HRID 579455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 579455
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:13]([C:16]1[S:17][C:18](B(O)O)=[CH:19][CH:20]=1)([OH:15])=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.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>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:18]3[S:17][C:16]([C:13]([OH:15])=[O:14])=[CH:20][CH:19]=3)[S:3][C:4]=2[CH:10]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27798075-Boronothiophene-2-carboxylic acidHCID 112187652-Bromo-6-methoxy-1,3-benzothiazole

Produkt 1

HCID 674500965-(6-Methoxy-benzothiazol-2-yl)-thiophene-2-carboxylic acidAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

2-Bromo-6-methoxy-benzothiazole (1.22 g, 5.00 mmol), 2-carboxythiophene-5-boronic acid (860 mg, 5.00 mmol), sodium carbonate (2.65 g, 25.00 mmol) and tetrakis(triphenylphosphine)palladium (300 mg, 0.25 mmol) were dissolved in a mixture of 80 mL N,N-dimethylformamide and 80 mL water. The mixture was stirred at 120° C. under argon for 2 h. The reaction mixture was evaporated and the residue was partitioned between 100 mL of water and 100 mL of dichloromethane. A considerable amount of white solid precipitated between the layers and was filtered off and triturated with diethyl ether, affording the title compound (550 mg, 1.89 mmol, 38%) as a white powder.

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. customthe residue was partitioned between 100 mL of water and 100 mL of dichloromethane
  3. customA considerable amount of white solid precipitated between the layers
  4. filtrationwas filtered off
  5. customtriturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3b8a9b163e4944ffac70392f51174513
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040714B2

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