Water → HCID 86718003, Verbindung

HRID 1500464Notizen

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 135 °C

Versuchsvorschrift

A mixture of 4-bromo-5-methyl-2,3-dihydrobenzofuran-7-amine (1e) (0.80 g, 3.5 mmol), pyridin-4-ylboronic acid (0.86 g, 7 mmol), Cs2CO3 (2.84 g, 8.7 mmol), Pd(PPh3)4 (0.40 g, 0.346 mmol) and water (7 mL) in DMF (35 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 (1f) as a yellow solid. MS-ESI (m/z): 227 (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-efc5e3350aa945acb5f09b467ebb132c
Quelldatensatz: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09206166B2

Notizen zur Reaktion

Wird geladen…