Water → HCID 86718011, Verbindung

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Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 135 °C

Versuchsvorschrift

The mixture of (R)-4-bromo-2,5-dimethyl-2,3-dihydrobenzofuran-7-amine (3g) (1.0 g, 4.3 mmol), pyridin-4-ylboronic acid (1.08 g, 8.77 mmol), Cs2CO3 (3.56 g, 10.9 mmol), Pd(PPh3)4 (0.506 g, 0.438 mmol) and water (9 mL) in DMF (44 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 (150 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 (3h) as a solid. MS-ESI (m/z): 241 (M+1)+.

Aufarbeitung

temperatureIt was cooled to ambient temperature
extractionextracted with EtOAc (150 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-94dbb8de730440d2aae66504afb3c61b
Quelldatensatz: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09206166B2

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