(+-)-2-Butanol → B-[2-[4-[(4-Phenyl-1-phthalazinyl)amino]phenoxy]-3-pyridinyl]boronic acid

HRID 227836

Reaktionsgleichung

Reaktionsgleichung von HRID 227836
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[C:12]([B:13]([OH:15])[OH:14])=[CH:11][CH:10]=[CH:9][N:8]=2)=[CH:4][CH:3]=1.Cl[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:21][N:20]=1.CC(O)CC>CCCCCC>[C:29]1([C:22]2[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:19]([NH:1][C:2]3[CH:17]=[CH:16][C:5]([O:6][C:7]4[C:12]([B:13]([OH:15])[OH:14])=[CH:11][CH:10]=[CH:9][N:8]=4)=[CH:4][CH:3]=3)=[N:20][N:21]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

5

Edukt 3

HCID 6568(+-)-2-ButanolHCID 2721091-Chloro-4-phenylphthalazineHCID 57756261HCID 57756261, Verbindung

Produkt 1

HCID 24856075B-[2-[4-[(4-Phenyl-1-phthalazinyl)amino]phenoxy]-3-pyridinyl]boronic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-(4-Aminophenoxy)pyridin-3-ylboronic acid (478 mg, 2.08 mmol), 1-chloro-4-phenylphthalazine (500 mg, 2.08 mmol) and butan-2-ol (4.16 ml, 2.08 mmol) were placed in a sealed tube. The reaction vessel was sealed and the mixture heated to 100° C. After 1 h 45 min, the reaction was cooled to rt. Hexane was added and the precipitated tan solid was filtered off with hexanes. LCMS of the solids indicated product, 2-(4-(4-phenylphthalazin-1-ylamino)phenoxy)pyridin-3-ylboronic acid. MS Calculated for C25H19BN4O: [M]+=434. Found: [M+1]+=435.

Aufarbeitung

  1. customThe reaction vessel was sealed
  2. temperaturethe reaction was cooled to rt
  3. filtrationthe precipitated tan solid was filtered off with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-244bc5c5788f46c08c78a7d4b12da76c
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560551B2

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