HCID 59511414, compound → HCID 59511431, compound

HRID 1157588Notes

Reaction equation

HRID 1157588 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].[H][H]>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

5

Reactant 2

HCID 59511414HCID 59511414, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59511431HCID 59511431, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

To a suspension of 2,2,2-trifluoro-N-[2-(methylsulfonyl)ethyl]-N-[(3-nitrophenyl)methyl]acetamide (0.88 g, 2.5 mmol) in i-PrOH was added 10% Pd/C (80 mg, 0.08 mmol). A balloon filled with hydrogen gas was installed, and the reaction was stirred vigorously at rt. After 64 h, the reaction mixture was filtered through celite, adsorbed onto silica gel, and purified by column chromatography to generate the title compound in 93% yield. 1H NMR (400 MHz, CDCl3) δ 7.17 (t, J=7.5 Hz, 1H), 6.60-6.67 (m, 2H), 6.53 (s, 1H), 4.62 (s, 2H), 3.73 (t, J=6.9 Hz, 2H), 3.18 (t, J=6.8 Hz, 2H), 2.92 (s, 3H). ES-LC/MS m/z=324 [M+H]+.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-5c9e1c6ba3cd49d49d160ffd8a23fee8
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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