Water → HCID 86718029, Verbindung

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Reaktionsgleichung

Br[C:2]1[C:7]2[CH2:8][CH:9]([CH2:11][O:12][CH3:13])[O:10][C:6]=2[C:5]([NH2:14])=[CH:4][C:3]=1[CH3:15].[N:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C.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>[CH3:13][O:12][CH2:11][CH:9]1[CH2:8][C:7]2[C:2]([C:19]3[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=3)=[C:3]([CH3:15])[CH:4]=[C:5]([NH2:14])[C:6]=2[O:10]1

Komponenten

Reaktionsbedingungen

Temperatur: 135 °C

Versuchsvorschrift

A mixture of 4-bromo-2-(methoxymethyl)-5-methyl-2,3-dihydrobenzofuran-7-amine (8c) (0.85 g, 3.1 mmol), pyridin-4-ylboronic acid (0.76 g, 6.2 mmol), Cs2CO3 (2.5 g, 7.8 mmol), Pd(PPh3)4 (0.18 g, 0.16 mmol) and water (6 mL) in DMF (20 mL) was stirred at 135° C. under N2 for 1 h. It was cooled to ambient temperature, poured into water (50 mL), extracted with EtOAc (60 mL), washed with water, brine, dried and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1 to 5:1 to 1:1) to give the title compound (8d) as a yellow oil. MS-ESI (m/z): 271 (M+1)+.

Aufarbeitung

temperatureIt was cooled to ambient temperature
extractionextracted with EtOAc (60 mL)
washwashed with water, brine
customdried
concentrationconcentrated
customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1 to 5:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag: ord-35aebdfb622a4a60ac57c4fdc531b0e1
Quelldatensatz: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09206166B2

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