Ammonium formate → HCID 22935586, compound

HRID 1272339Notes

Reaction equation

HRID 1272339 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]([CH3:34])=[C:16]([CH3:33])[C:17]3[O:21][C:20]([CH3:23])([CH3:22])[CH:19]([C:24]4[CH:25]=[N:26][C:27]([F:30])=[CH:28][CH:29]=4)[C:18]=3[C:31]=2[CH3:32])[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[C].[Pd]>[F:30][C:27]1[N:26]=[CH:25][C:24]([CH:19]2[C:18]3[C:31]([CH3:32])=[C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[C:15]([CH3:34])=[C:16]([CH3:33])[C:17]=3[O:21][C:20]2([CH3:23])[CH3:22])=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 22935580HCID 22935580, compound

Product 1

HCID 22935586HCID 22935586, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 10% palladium carbon (50% water, 183 mg), 4-benzyl-1-(3-(6-fluoropyridine-3-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)piperazine (1.83 g, 4 mmol) obtained in Example 126 and ammonium formate (505 mg, 8 mmol) in methanol (50 ml) was refluxed for 2 hours under nitrogen atmosphere. The resulting mixture was cooled to room temperature and the catalyst was removed by filtration. The filtrate was concentrated under reduced pressure. The residue was diluted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified with basic silica gel column chromatography (ethyl acetate) to obtain 1.3 g (yield 88%) of the title compound as an amorphous powder.

Workup

  1. temperaturewas refluxed for 2 hours under nitrogen atmosphere
  2. customthe catalyst was removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified with basic silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-9bce49612edf43caa47adf6e3bc1b2c0
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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