Sodium Carbonate → 4-(2-Amino-5-chloropyridin-3-yl)phenol

HRID 1405722Notizen

Reaktionsgleichung

C(=O)([O-])[O-].[Na+].[Na+].[Si:7]([O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].Br[C:25]1[C:26]([NH2:32])=[N:27][CH:28]=[C:29]([Cl:31])[CH:30]=1>COCCOC.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>[NH2:32][C:26]1[C:25]([C:18]2[CH:17]=[CH:16][C:15]([OH:14])=[CH:20][CH:19]=2)=[CH:30][C:29]([Cl:31])=[CH:28][N:27]=1.[Si:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:25]2[C:26]([NH2:32])=[N:27][CH:28]=[C:29]([Cl:31])[CH:30]=2)=[CH:17][CH:16]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of sodium carbonate (4.09 g), tetrakis(triphenylphosphine)palladium(0) (0.668 g), 4-(tert-butyldimethylsilyloxy)phenylboronic acid (6.32 g) and 3-bromo-5-chloropyridin-2-amine (4.00 g) in DME (100 mL) and water (20 mL) was stirred at 80° C. overnight. Silica gel was added and the mixture was concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give 4-(2-amino-5-chloropyridin-3-yl)phenol (3.05 g) as a pale yellow solid and 3-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-5-chloropyridin-2-amine (1.55 g) as a yellow solid.

Aufarbeitung

additionSilica gel was added
concentrationthe mixture was concentrated in vacuo
customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag: ord-973c39f7fefb4bc4beb7234e933c5251
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08916551B2

Notizen zur Reaktion

Wird geladen…