Methyl iodide → Methyl 1,2-dimethyl-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydropyridine-3-carboxylate

HRID 734707Notes

Reaction equation

[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]2[C:17]([O:19][CH3:20])=[O:18])=[CH:5][CH:4]=1.[H-].[Na+].[CH3:25]I>CN(C=O)C>[CH3:25][N:12]1[C:13](=[O:15])[CH2:14][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:21])([F:1])[F:22])=[CH:8][CH:7]=2)[C:10]([C:17]([O:19][CH3:20])=[O:18])=[C:11]1[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

The product from Example 5, Step 1 (200 mg, 0.638 mmol, 1.0 equiv) dissolved in 3.0 mL DMF was cooled to 0° C. in an ice bath. NaH (26 mg, 0.638 mmol, 1.0 equiv) and MeI (0.040 mL, 0.638 mmol, 1.0 equiv) were added, and the reaction mixture was warmed to room temperature over 1 hr. After 1 hr, more NaH (13 mg, 0.319 mmol, 0.5 equiv) and MeI (0.020 mL, 0.319 mmol, 0.5 equiv) were added to the reaction mixture and stirred at room temperature for 45 min. The reaction was quenched with water and diluted with EtOAc. The phases were separated, and the organic phase was washed once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo to provide 209 mg (100%) of the title compound as a clear oil. MS (ES+) m/e 328 [M+H]+

Workup

temperaturethe reaction mixture was warmed to room temperature over 1 hr
customThe reaction was quenched with water
additiondiluted with EtOAc
customThe phases were separated
washthe organic phase was washed once with satd
dry with materialThe organic phase was dried over Na2SO4
filtrationfiltered
concentrationconcentrated en vacuo

Sources & evidence

ORD record: ord-59bab29145104c48b886a830045381de
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592357B2

Reaction notes

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