Reaktionsgleichung
Br[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=1.[C:11]1(B(O)O)[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C(Cl)Cl.[Pd](Cl)Cl>[C:11]1([C:2]2[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][CH:3]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
Under an atmosphere of nitrogen, a solution of 6-bromo-pyridine-2-carboxylic acid (CAN 1190-87-4, 3 g, 6.4 mol), cyclohexenylboronic acid (CAN 21190-87-4, 0.89 g, 7.1 mmol), 1,1′-bis(diphenyl-phosphino)ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464-05-4, 8 mg, 0.13 mmol), potassium carbonate (1.78 g, 12.9 mmol) in H2O (30 mL) was heated to 100° C. overnight. The reaction mixture was extracted with ethyl acetate (50 mL). The pH of the aqueous layer was adjusted to 5 by addition of 1 N hydrochloric acid and the resulting mixture was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by prep-HPLC to yield the title compound (0.8 g, 3.94 mmol, 61.2%) as yellow oil; MS (EI): m/e=204.2 [M+H]+.
Aufarbeitung
- extractionThe reaction mixture was extracted with ethyl acetate (50 mL)
- additionThe pH of the aqueous layer was adjusted to 5 by addition of 1 N hydrochloric acid
- extractionthe resulting mixture was extracted with ethyl acetate (3×50 mL)
- washThe combined organic extracts were washed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- customevaporated
- customThe residue was purified by prep-HPLC
Quellen und Nachweise
- ORD-Eintrag
- ord-ac3348b122cb4e65b8dda49c5b962d1c
- Quelldatensatz
- uspto-grants-2016_04
- Patentnummer
- US09321727B2
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