Potassium Carbonate → HCID 57809771, compound

HRID 2106006Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:30][CH3:31])=[C:6]([C:8]([CH3:29])([CH3:28])[CH2:9][C:10]([OH:27])(C(F)(F)F)[CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[CH:14]=[CH:13]2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:30][CH3:31])=[C:6]([C:8]([CH3:29])([CH3:28])[CH2:9][C:10](=[O:27])[CH2:11][N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:22])[CH:14]=[CH:13]2)[CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-quinolin-4-one (2.25 g, 5.14 mmol) in DMF (40 mL) was added potassium carbonate (2.13 g, 15.4 mmol) followed by heating to 120° C. in a sealed reaction vessel for 14 hours. The solution was diluted with 300 mL of diethyl ether, washed with one 200 mL portion of saturated aqueous sodium bicarbonate, three 100 mL portions of water, one 100 mL portion of brine, dried over anhydrous sodium sulfite (Na2SO3), and concentrated in vacuo. The crude material was purified by flash column chromatography (5% MeOH/CH2Cl2) to give 1-[4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-oxopentyl]-1H-quinolin-4-one as a brown foam (1.07 g, 57%).

Workup

washwashed with one 200 mL portion of saturated aqueous sodium bicarbonate, three 100 mL portions of water, one 100 mL portion of brine
dry with materialdried over anhydrous sodium sulfite (Na2SO3)
concentrationconcentrated in vacuo
customThe crude material was purified by flash column chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-b56f1c4c66f1458db915ade2839b05fc
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579469B2

Reaction notes

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