Methanol → HCID 59598165, compound

HRID 2266020Notes

Reaction equation

HRID 2266020 reaction equation
[C:1]([C:3]1[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:4]=1[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6])#[CH:2].CO>[Pd]>[CH2:1]([C:3]1[N:14]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:12]=[CH:11][C:4]=1[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 86625533HCID 86625533, compound

Product 1

HCID 59598165HCID 59598165, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumSolvent

Procedure

To a suspension of 2-ethynyl-N-methoxy-N-methyl-6-trifluoromethyl-nicotinamide (145 mg, 0.561 mmol) in 5% Pd/C (30 mg) was added CH3OH (4 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 2-ethyl-N-methoxy-N-methyl-6-trifluoromethyl-nicotinamide (112 mg, 76%).

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-452c990b363842688efebd6349a2018b
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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