Triethylamine → 3-Ethyl 5-methyl 6-(difluoromethyl)-4-(2-methylaziridinyl)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

HRID 1763148Notes

Reaction equation

HRID 1763148 reaction equation
Cl[C:2]([F:27])([F:26])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([N:18]2[CH2:20][CH:19]2[CH3:21])[C:4]=1[C:22]([O:24][CH3:25])=[O:23].C(N(CC)CC)C>C(O)C.[Pd]>[F:27][CH:2]([F:26])[C:3]1[N:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([N:18]2[CH2:20][CH:19]2[CH3:21])[C:4]=1[C:22]([O:24][CH3:25])=[O:23]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 140138283-Ethyl 5-methyl 6-(chlorodifluoromethyl)-4-(2-methylaziridinyl)-2-(trifluoromethyl)-3,5-pyridinedicarboxylate

Product 1

HCID 140138303-Ethyl 5-methyl 6-(difluoromethyl)-4-(2-methylaziridinyl)-2-(trifluoromethyl)-3,5-pyridinedicarboxylateYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2.5 g (0.0059 mol) of product of Example 81, 0.6 g (0.0059 mol) of triethylamine and 0.25 g of 5% Pd/C (50% water coated) in 100 ml of ethanol was hydrogenated (446 kPa, for 18 hours at 50° C. The mixture was then filtered through celite and concentrated in vacuo to remove the ethyl alcohol. The residue was poured into water, and extracted with diethyl ether. The ether extract was washed with water, then dried over MgSO4. The dry ether phase was then concentrated in vacuo to yield 2.00 g of a yellow solid. This solid was then recrystallized in hexane to yield 1.28 g (56%) of product as a tan solid; mp 61° C.

Workup

  1. filtrationThe mixture was then filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customto remove the ethyl alcohol
  4. additionThe residue was poured into water
  5. extractionextracted with diethyl ether
  6. extractionThe ether extract
  7. washwas washed with water
  8. dry with materialdried over MgSO4
  9. concentrationThe dry ether phase was then concentrated in vacuo

Sources & evidence

ORD record
ord-2ccedc8bd9fb40ef8d80391cd86772e7
Source dataset
uspto-grants-1989_05
Patent number
US04835279

Reaction notes

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