2-Methylpyridine → HCID 10237071, compound

HRID 1988152Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].C([Li])(C)(C)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:29])([CH3:28])[CH2:21][C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])=[CH:16][CH:15]=1>C1COCC1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:29])([CH3:28])[CH2:21][C:22]([CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)([OH:27])[C:23]([F:25])([F:26])[F:24])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of 2-picoline in 1 mL of THF was cooled down to −78° C. tert-Butyl lithium (1.7 M in pentanes, 0.2 mL (0.34 mmol)) was added dropwise over 5 minutes. The mixture stirred at −78° C. for 15 minutes, and then a solution of 40 mg of 4-(4-chlorophenyl)-1,1,1-trifluoro-4-methylpentan-2-one in 0.5 mL of THF was added. Stirring continued at −78° C. for 20 minutes. The reaction was quenched with 0.5 N HCl and extracted three times with EtOAc. The organic layers were combined and washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography to yield 9.6 mg of the title compound as a light yellowish oil.

Workup

additionwas added dropwise over 5 minutes
stirringStirring
waitcontinued at −78° C. for 20 minutes
customThe reaction was quenched with 0.5 N HCl
extractionextracted three times with EtOAc
washwashed with water, brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-84279621e8a442fc8999b228f3798628
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07553966B2

Reaction notes

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