Methanol → HCID 86625536, compound

HRID 2266024Notes

Reaction equation

HRID 2266024 reaction equation
[CH3:1][O:2][N:3]([CH3:21])[C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[N:7][C:6]=1[C:15]#[C:16][CH2:17][O:18][CH3:19].CO>[Pd]>[CH3:1][O:2][N:3]([CH3:21])[C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[N:7][C:6]=1[CH2:15][CH2:16][CH2:17][O:18][CH3:19]

Participants

4

Reactant 2

HCID 887MethanolHCID 86625535HCID 86625535, compound

Product 1

HCID 86625536HCID 86625536, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 23938PalladiumSolvent

Procedure

To a suspension of N-methoxy-2-(3-methoxy-prop-1-ynyl)-N-methyl-6-trifluoromethyl-nicotinamide (247 mg, 0.817 mmol) in 5% Pd/C (50 mg) was added CH3OH (6 ml). The mixture was purged three times with hydrogen gas (50 psi) and shaken for 2 hours at room temperature. The reaction mixture was filtered over a pad of Celite and concentrated under reduced pressure. The crude residue was chromatographed to yield the N-methoxy-2-(3-methoxy-propyl)-N-methyl-6-trifluoromethyl-nicotinamide (160 mg, 64%).

Workup

  1. customThe mixture was purged three times with hydrogen gas (50 psi)
  2. filtrationThe reaction mixture was filtered over a pad of Celite
  3. concentrationconcentrated under reduced pressure
  4. customThe crude residue was chromatographed

Sources & evidence

ORD record
ord-4e3e8ceeed544f6faf37e332e9e72985
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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