2-Fluoro-6-(trifluoromethyl)benzaldehyde → 3-Methyl 5-(1-methylethyl) 2-(fluoromethyl)-4-(2-fluoro-6-(trifluoromethyl)phenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylate

HRID 1789013Notes

Reaction equation

HRID 1789013 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:3]=1[CH:4]=O.[F:14][CH2:15][C:16](=O)[CH2:17][C:18]([O:20][CH3:21])=[O:19].[NH2:23][C:24]([CH3:32])=[CH:25][C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27]>>[F:14][CH2:15][C:16]1[NH:23][C:24]([CH3:32])=[C:25]([C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27])[CH:4]([C:3]2[C:6]([C:10]([F:13])([F:12])[F:11])=[CH:7][CH:8]=[CH:9][C:2]=2[F:1])[C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

4

Reactant 3

HCID 5219332-Fluoro-6-(trifluoromethyl)benzaldehydeHCID 3271821Isopropyl3-aminocrotonateHCID 14170515Methyl 4-fluoro-3-oxobutanoate

Product 1

HCID 141705343-Methyl 5-(1-methylethyl) 2-(fluoromethyl)-4-(2-fluoro-6-(trifluoromethyl)phenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylateYield 3%

Procedure

2-Fluoro-6-(trifluoromethyl)benzaldehyde (1.51 g, 7.8 mmoles), methyl 4-fluoro-3-oxobutanoate (1.06 g, 7.8 mmoles) and 1-methylethyl 3-amino-2-butenoate (1.13 g, 7.8 mmoles) were heated at 90° under nitrogen with stirring for 2 hours. The cooled reaction mixture was chromatographed twice; first eluting with toluene/ethyl acetate mixtures and then with ethyl acetate/petroleum ether (60°-80°) mixtures. The title compound (0.1 g) was obtained on evaporation of the pure fractions mp 82°-4°.

Workup

  1. customThe cooled reaction mixture
  2. customwas chromatographed twice
  3. washfirst eluting with toluene/ethyl acetate mixtures
  4. customwith ethyl acetate/petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-bb19e9b64f2446549da75cfab4f3bd94
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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