Ammonium formate → HCID 23114142, compound

HRID 2376478Notes

Reaction equation

HRID 2376478 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:18]3[O:17][CH2:16][CH:15]([C:19]4[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=4)[C:14]=3[C:13]([CH3:28])=[C:12]([NH:29][C:30](=[O:36])[CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:11]=2[CH3:37])[CH:7]=[CH:8][CH:9]=1)([O-])=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[C:18]3[O:17][CH2:16][CH:15]([C:19]4[CH:24]=[CH:23][C:22]([CH:25]([CH3:26])[CH3:27])=[CH:21][CH:20]=4)[C:14]=3[C:13]([CH3:28])=[C:12]([NH:29][C:30](=[O:36])[CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:11]=2[CH3:37])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 23114166HCID 23114166, compound

Product 1

HCID 23114142HCID 23114142, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of N-(7-(3-nitrophenyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (2.50 g, 5 mmol) obtained in Example 109 and ammonium formate (1.26 g, 20 mmol) in ethanol (50 mL) was added 10% palladium on carbon (water content: 50%, 0.25 g), and the resulting mixture was heated at 65° C. and stirred for 2 hours. The reaction solution was cooled to room temperature, the catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The extracts were washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to obtain 2.15 g (yield: 92%) of the title compound. Melting point: 170-172° C. (ethyl acetate-hexane).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe extracts were washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-dc9db8cf84564502a3e3218bcf873375
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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