Pyridine → (S)-1-(6-bromo-2-methyl-5-(3-methylpyridin-2-yloxy)-3,4-dihydroquinolin-1(2H)-yl)ethanone

HRID 1051661Notes

Reaction equation

[Br:1][C:2]1[C:3]([OH:16])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:14])[CH3:13])[C@@H:7]([CH3:15])[CH2:6][CH2:5]2.N1C=CC=CC=1.[CH3:23][C:24]1[C:25](B(O)O)=[N:26][CH:27]=[CH:28][CH:29]=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CN(C)C=O>[Br:1][C:2]1[C:3]([O:16][C:25]2[C:24]([CH3:23])=[CH:29][CH:28]=[CH:27][N:26]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:14])[CH3:13])[C@@H:7]([CH3:15])[CH2:6][CH2:5]2

Participants

Conditions

Temperature: 90 °C

Procedure

A 100-mL, round-bottom flask equipped with a balloon filled with air was charged with (S)-1-(6-bromo-5-hydroxy-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone (0.200 g, 0.70 mmol), pyridine (1 mL), copper (II) acetate (0.382 g, 2.10 mmol), 3-methylpyridin-2-ylboronic acid 0.190 g, 1.39 mmol) and N,N-dimethylformamide (8 mL). The resulting mixture stirred at 90° C. overnight. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was concentrated under vacuum. The residue was purified by column chromatography on silica gel (eluting with 1:8, ethyl acetate/petroleum ether) to afford (S)-1-(6-bromo-2-methyl-5-(3-methylpyridin-2-yloxy)-3,4-dihydroquinolin-1(2H)-yl)ethanone (0.129 g, 49%) as yellow oil. MS (ESI, pos. ion) m/z 375, 377 [M+H]+.

Workup

customA 100-mL, round-bottom flask equipped with a balloon
additionfilled with air
temperatureAfter cooling to room temperature
filtrationthe reaction mixture was filtered
concentrationthe filtrate was concentrated under vacuum
customThe residue was purified by column chromatography on silica gel (eluting with 1:8, ethyl acetate/petroleum ether)

Sources & evidence

ORD record: ord-55efb092b94d41e0958658ce41bef31c
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388161B2

Reaction notes

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