Triethylamine → HCID 53990096, compound

HRID 1761331Notes

Reaction equation

HRID 1761331 reaction equation
Cl[C:2]([F:28])([F:27])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:5]([CH:24]([CH3:26])[CH3:25])[N:4]=1.C(N(CC)CC)C>C(O)C.[Pd]>[F:28][CH:2]([F:27])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:5]([CH:24]([CH3:26])[CH3:25])[N:4]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 53697729HCID 53697729, compound

Product 1

HCID 53990096HCID 53990096, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 17 g (40 mmol) of crude 3-methyl 5-(1,1-dimethylethyl) 2-(chlorodifluoromethyl)-6-(1-methylethyl)-4-(2-methylpropyl)-3,5-pyridinedicarboxylate and 7 mL of triethylamine in 160 mL of ethanol was subjected to hydrogenolysis at ambient temperature and 2 atom pressure in the presence of 3 g of 5% palladium on charcoal for 18 hours. The suspension was filtered through celite and concentrated. Water and CH2Cl2 were added. The CH2Cl2 layer was separated, washed with H2O, dried and concentrated. Column chromatography on silica gel (2% ethyl acetate/cyclohexane) gave 14 g (91%) of 5-(1,1-dimethylethyl) 3-methyl 2-(difluoromethyl)-6-(1-methylethyl)-4-(2-methylpropyl)-3,5-Pyridinedicarboxylate as colorless oil, nD25 1.4713.

Workup

  1. customwas subjected to hydrogenolysis at ambient temperature
  2. filtrationThe suspension was filtered through celite and
  3. concentrationconcentrated
  4. additionWater and CH2Cl2 were added
  5. customThe CH2Cl2 layer was separated
  6. washwashed with H2O
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3fbdf3f82b214203b2f771ccaa2542be
Source dataset
uspto-grants-1989_05
Patent number
US04826532

Reaction notes

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