Water → Methyl 7-(4-hydroxyphenyl)-4-quinolinecarboxylate

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Reaktionsgleichung

Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O>[OH:30][C:27]1[CH:28]=[CH:29][C:24]([C:2]2[CH:11]=[C:10]3[C:5]([C:6]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:8]=[N:9]3)=[CH:4][CH:3]=2)=[CH:25][CH:26]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A mixture of 160 mg (0.60 mmol) of methyl 7-bromo-4-quinolinecarboxylate, 200 mg (0.90 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 7 mg (0.03 mmol) of palladium(II)acetate, 16 mg (0.06 mmol) of triphenylphosphine, 450 mg (2.10 mmol) of K3PO4 and 50 uL (3.01 mmol) of H2O in 3 mL of dioxane was stirred at 60° C. for 1.5 hr. EtOAc was added then the organics were washed with H2O and brine then concentrated. The residue was suspended in cold EtOAc and the solids were collected by suction filtration, washed with cold EtOAc and dried to give 92 mg (55%) of methyl 7-(4-hydroxyphenyl)-4-quinolinecarboxylate as a tan solid. 1H NMR (400 MHz, CDCl3): δ 9.75 (s, 1H), 9.03 (s, 1H), 8.63 (d, J=9 Hz, 1H), 8.25 (d, J=2 Hz, 1H), 8.03 (dd, JA=2 Hz, JB=9 Hz, 1H), 7.87 (s, 1H), 7.72 (d, J=8 Hz, 2H), 6.90 (d, J=8 Hz, 2H), 3.98 (s, 3H). ESI-LCMS m/z 280 (M+H)+.

Aufarbeitung

washthe organics were washed with H2O and brine
concentrationthen concentrated
filtrationthe solids were collected by suction filtration
washwashed with cold EtOAc
customdried

Quellen und Nachweise

ORD-Eintrag: ord-e73e2523f1cd4f8f86d67b0637673ba0
Quelldatensatz: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07960552B2

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