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

HRID 2423401Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

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)+.

Workup

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

Sources & evidence

ORD record: ord-e73e2523f1cd4f8f86d67b0637673ba0
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960552B2

Reaction notes

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