Sodium ethoxide → HCID 57809785, compound

HRID 2106009Notes

Reaction equation

[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[F:13][C:14]1[CH:15]=[CH:16][C:17]([O:31][CH3:32])=[C:18]([C:20]([CH3:30])([CH3:29])[CH2:21][C:22]2([C:25]([F:28])([F:27])[F:26])[CH2:24][O:23]2)[CH:19]=1.[O-]CC.[Na+]>C(O)C>[F:13][C:14]1[CH:15]=[CH:16][C:17]([O:31][CH3:32])=[C:18]([C:20]([CH3:29])([CH3:30])[CH2:21][C:22]([OH:23])([C:25]([F:28])([F:27])[F:26])[CH2:24][N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:11](=[O:12])[C:2]([CH3:1])=[CH:3]2)[CH:19]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 3-methyl-1H-quinolin-4-one (0.76 g), 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (0.089 g) and sodium ethoxide in ethanol (0.18 mL of a 21 wt. % solution) in 2 mL of anhydrous ethanol was heated at 85° C. for 12 hours, cooled to room temperature, and most of the volatiles removed in vacuo. The residue was diluted with diethyl ether and methanol and washed with water and brine, and dried over magnesium sulfate. The residue was purified by flash silica gel chromatography using ethyl acetate as the eluent. The product-rich fractions were concentrated in vacuo and dried to afford 1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-3-methyl-1H-quinolin-4-one, m.p. >225° C.

Workup

temperaturecooled to room temperature
custommost of the volatiles removed in vacuo
additionThe residue was diluted with diethyl ether and methanol
washwashed with water and brine
dry with materialdried over magnesium sulfate
customThe residue was purified by flash silica gel chromatography
concentrationThe product-rich fractions were concentrated in vacuo
customdried

Sources & evidence

ORD record: ord-e7cd670c28e1425f831cf0e4fbadd966
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579469B2

Reaction notes

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