Formate → HCID 136454817, compound

HRID 1743995Notes

Reaction equation

HRID 1743995 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:31])=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([O:23]CC3C=CC=CC=3)=[CH:15][CH:14]=2)[N:8]=1.C([O-])=O.[NH4+].C([O-])=O>[Pd].C(O)C>[CH3:1][C:2]1[NH:3][C:4]([CH3:31])=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([OH:23])=[CH:15][CH:14]=2)[N:8]=1

Participants

6

Reactant 3

HCID 283FormateHCID 2723923Ammonium formateHCID 54024829HCID 54024829, compound

Product 1

HCID 136454817HCID 136454817, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a 125 mL round-bottomed flask equipped with condenser and N2 inlet were added 1.53 g (3.795 mmol) 2-(2,5-dimethylpyrrolyl)-6-(4-benzyloxy-1-naphthyl)-pyridine, 1.20 g (18.975 mmol) ammonium formate, 100 mg 10% palladium-on-carbon, and 30 mL ethanol. The reaction was refluxed 4 hours, with additional catalyst and formate added at 2 and 3 hours, then cooled and filtered through Celite with ethanol and methylene chloride. The filtrate was evaporated and the residue taken up in ethyl acetate/aqueous sodium bicarbonate solution. The organic layer was washed with brine, dried over sodium sulfate, and evaporated to a light brown solid, 1.21 g (˜100%).

Workup

  1. customTo a 125 mL round-bottomed flask equipped with condenser and N2 inlet
  2. additionadded at 2 and 3 hours
  3. temperaturecooled
  4. filtrationfiltered through Celite with ethanol and methylene chloride
  5. customThe filtrate was evaporated
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated to a light brown solid, 1.21 g (˜100%)

Sources & evidence

ORD record
ord-86be839d7d0d4a41925f3f6d1607f926
Source dataset
uspto-grants-2006_03
Patent number
US07012078B2

Reaction notes

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