Boric Acid → HCID 136407394, Verbindung

HRID 562921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 562921
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[C:23]([CH:28]=[CH:29][N:30]=3)[C:24]([O:26][CH3:27])=[O:25])=[CH:17][C:16]=2[C:31]#[N:32])=[CH:11][C:10]=1[C:33]#[N:34])C1C=CC=CC=1.B(O)(O)O.C(C1C=C(C2C=C(C=CN=2)C(OC)=O)C=CC=1OS(C(F)(F)F)(=O)=O)#N.[H][H]>C1COCC1.CO.[C].[Pd]>[C:31]([C:16]1[CH:17]=[C:18]([C:21]2[CH:22]=[C:23]([CH:28]=[CH:29][N:30]=2)[C:24]([O:26][CH3:27])=[O:25])[CH:19]=[CH:20][C:15]=1[C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([C:33]#[N:34])[CH:11]=1)#[N:32]

Komponenten

8

Edukt 4

HCID 7628Boric AcidHCID 66995426HCID 66995426, VerbindungHCID 86616562Methyl 2-(3-cyano-4-([(trifluoromethyl)sulfonyl]oxy)phenyl)isonicotinateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 136407394HCID 136407394, VerbindungAusbeute 47,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.32 g of methyl 2-[4′-(benzyloxy)-2,3′-dicyanobiphenyl-4-yl]isonicotinate, which had been obtained in the same manner as in Preparation Example 8(1) using 4-(benzyloxy)-3-cyanophenyl]boric acid and methyl 2-(3-cyano-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)isonicotinate, was dissolved in a mixture of 50 ml of THF and 50 ml of methanol, and 0.5 g of palladium-carbon was added, followed by stirring in a hydrogen atmosphere at room temperature for 12 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain 0.5 g of methyl 2-(2,3′-dicyano-4′-hydroxybiphenyl-4-yl)isonicotinate. (2) 230 mg of this compound was dissolved in DMF, and 50 μL of iodomethane and 108 mg of potassium carbonate were added, followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried and concentrated under reduced pressure. Chloroform was added to the residue, and the precipitated crystal was collected by filtration, followed by washing with chloroform to obtain 73 mg of methyl 2-(2,3′-dicyano-4′-methoxybiphenyl-4-yl)isonicotinate. (3) 73 mg of this compound was dissolved in 2 ml of methanol and 2 ml of THF, and 220 μL of an aqueous 1 M sodium hydroxide solution was added, followed by heating at 60° C. for 2 hours. After cooling, the solvent was removed under reduced pressure, and then water was added to the residue, followed by neutralization with 1 M hydrochloric acid. The precipitated crystal was collected by filtration and washed with a mixture of ethanol and water to obtain 64 mg of 2-(2,3′-dicyano-4′-methoxybiphenyl-4-yl)isonicotinic acid.

Aufarbeitung

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e994d74e0aab4de9873a64af1cb8cce0
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067446B2

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