Potassium Carbonate → 7-Chloro-5-(4-chlorophenyl)-2-methylquinolin-6-ol

HRID 931700Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

Pd(PPh3)4 (120 mg, 0.1 mmol) was added to a mixture of 5-bromo-7-chloro-2-methylquinolin-6-ol (1D) (345 mg, 1.04 mmol), 4-chlorophenylboronic acid (326 mg, 2.09 mmol) and K2CO3 (2.3 mL 2 M in water, 4.7 mmol) in 1,2-dimethoxyethane (10 mL). The reaction mixture was flushed with nitrogen, heated at 80° C. for 16 hours, and then the volatile component was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with a NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide 1E as a white solid (147 mg, 47%). LCMS-ESI+ (m/z): 304.2, 306.2 (M+H)+.

Workup

customThe reaction mixture was flushed with nitrogen
customthe volatile component was removed in vacuo
dissolutionThe residue was dissolved in ethyl acetate (100 mL)
washwashed with a NaHCO3 solution, water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe obtained residue was purified by flash chromatography

Sources & evidence

ORD record: ord-d64f9ff075f249de8fd4cc5daf84b5e4
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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