Benzo(B)Thiophene-2-Boronic Acid → 5-(1-Benzothien-2-yl)pyridine-2-carboxamide

HRID 501049

Reaktionsgleichung

Reaktionsgleichung von HRID 501049
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1B(O)O.Br[C:14]1[CH:15]=[CH:16][C:17]([C:20]([NH2:22])=[O:21])=[N:18][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:14]1[CH:15]=[CH:16][C:17]([C:20]([NH2:22])=[O:21])=[N:18][CH:19]=1

Komponenten

6

Edukt 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 11430Potassium CarbonateHCID 7351515-Bromopyridine-2-carboxamide

Produkt 1

HCID 250149305-(1-Benzothien-2-yl)pyridine-2-carboxamideAusbeute 3,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Benzothienylboronic acid (1.8 mmol), 5-bromopyridine-2-carboxamide (1.2 mmol), 2M K2CO3 (2.4 mL), Pd(dppf)Cl2 (0.12 mmol) were mixed and stirred at 80° C. in DMF for 3 h. The reaction mixture was filtered and to the filtrated was added EtOAc and H2O. The layers were separated and the aqueous phase was extracted twice with EtOAc. The organic extracts were dried over Na2SO4. The solvent was evaporated in vacuo to give a brown solid. The crude was subjected to reverse phase HPLC to afford the title compound as a light brown solid (11 mg). 1H NMR δ ppm 9.07 (d, 1 H) 8.34 (dd, 1 H) 8.24-8.02 (m, 5 H) 7.73 (s br, 1 H) 7.54-7.37 (m, 2 H); MS m/z 255 (M+H).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered and to the filtrated
  2. additionwas added EtOAc and H2O
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted twice with EtOAc
  5. dry with materialThe organic extracts were dried over Na2SO4
  6. customThe solvent was evaporated in vacuo
  7. customto give a brown solid

Quellen und Nachweise

ORD-Eintrag
ord-a032e3afb19e418595dd11b2e977e424
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772256B2

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