HCID 22128978, compound → HCID 22128977, compound

HRID 1858362Notes

Reaction equation

HRID 1858362 reaction equation
[NH2:1][C:2]1[C:29]([N+:30]([O-])=O)=[CH:28][CH:27]=[CH:26][C:3]=1[O:4][CH2:5][CH2:6][N:7]([CH2:14][CH2:15][CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:8](=[O:13])[C:9]([F:12])([F:11])[F:10]>C(O)C.[Pd]>[NH2:1][C:2]1[C:29]([NH2:30])=[CH:28][CH:27]=[CH:26][C:3]=1[O:4][CH2:5][CH2:6][N:7]([CH2:14][CH2:15][CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:8](=[O:13])[C:9]([F:10])([F:11])[F:12]

Participants

4

Reactant 1

HCID 22128978HCID 22128978, compound

Product 1

HCID 22128977HCID 22128977, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution containing N-[2-(2-amino-3-nitro-phenoxy)-ethyl]-2,2,2-trifluoro-N-[3-(1H-indol-3-yl)-propyl]-acetamide (3.86 g, 8.57 mmol) in ethanol (40 ml) under nitrogen was added 10% palladium on carbon (1 g). The mixture was hydrogenated at 40 psi for 6 hours. The catalyst was filtered, washed with ethanol and the filtrate was concentrated to give the crude product. Purification by chromatography (40% ethyl acetate-hexanes) afforded 2.8 g (78.8%) of product as a viscous brown oil; MS EI m/e 420 (M+).

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with ethanol
  3. concentrationthe filtrate was concentrated
  4. customto give the crude product
  5. customPurification by chromatography (40% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-9c8e47c147ac4b16bb7627a38676e7f9
Source dataset
uspto-grants-2000_11
Patent number
US06150533

Reaction notes

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