HCID 59511414, compound → HCID 59511431, compound

HRID 1159995Notes

Reaction equation

HRID 1159995 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([N:5]([CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1)=[O:4]>CC(O)C.[Pd]>[NH2:13][C:9]1[CH:8]=[C:7]([CH2:6][N:5]([CH2:16][CH2:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:3](=[O:4])[C:2]([F:23])([F:1])[F:22])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 59511414HCID 59511414, compound

Product 1

HCID 59511431HCID 59511431, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of 2,2,2-trifluoro-N-[2-(methylsulfonyl)ethyl]-N-[(3-nitrophenyl)methyl]acetamide (0.88 g, 2.5 mmol) in 2-propanol (75 mL) was added 10% Pd/C (80 mg). The reaction was stirred at rt under a hydrogen atmosphere (1 atm) for 72 h. The reaction mixture was filtered through Celite, adsorbed to silica, and purified by column chromatography to generate the title compound in 93% yield (0.75 g, 2.3 mmol). 1H NMR (400 MHz, CDCl3): δ 7.17 (t, J=7.9 Hz, 1H), 6.66 (d, J=6.9 Hz, 1H), 6.61 (d, J=7.7 Hz, 1H), 6.53 (s, 1H), 4.62 (s, 2H), 3.72-3.77 (m, 4H), 3.18 (t, J=6.8 Hz, 2H), 3.01 (s, 3H). MS (ESI) m/z=324 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-43e60ae607414ed09190c97d52dfdb76
Source dataset
uspto-grants-2010_10
Patent number
US07812022B2

Reaction notes

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