2,4,6-Trimethylpyridine → HCID 10194276, compound

HRID 2080572Notes

Reaction equation

C([Li])(C)(C)C.[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH3:14])[N:8]=1.[F:15][C:16]([F:33])([F:32])[C:17](=[O:31])[CH2:18][C:19]([C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[O:29][CH3:30])([CH3:21])[CH3:20]>C1COCC1>[F:33][C:16]([F:15])([F:32])[C:17]([CH2:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH3:14])[N:8]=1)([OH:31])[CH2:18][C:19]([C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[O:29][CH3:30])([CH3:21])[CH3:20]

Participants

Conditions

Temperature: -70 °C

Procedure

tert-Butyl lithium (1.7 M in pentane, 0.5 mL) was added dropwise to a solution of 2,4,6-trimethylpyridine (0.12 g) in THF (0.5 mL) cooled to −70° C. under argon. The mixture was stirred at −70° C. for 15 minutes and 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one (0.10 g) (Example 1) in THF (0.5 mL) was added. The reaction mixture was stirred for 20 minutes and then quenched with acetic acid. The mixture was diluted with EtOAc, washed with water, dried, filtered, and concentrated in vacuo. Fractionation by preparative layer chromatography on silica gel (methylene chloride-hexanes) followed by crystallization gave 43 mg of the title compound, m.p. 95° C.-98° C.

Workup

stirringThe reaction mixture was stirred for 20 minutes
customquenched with acetic acid
additionThe mixture was diluted with EtOAc
washwashed with water
customdried
filtrationfiltered
concentrationconcentrated in vacuo
customFractionation by preparative layer chromatography on silica gel (methylene chloride-hexanes) followed by crystallization

Sources & evidence

ORD record: ord-3314cd5d1eac4514b229fc345e66e284
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932392B2

Reaction notes

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