HCID 68540106, compound → HCID 59134449, compound

HRID 1993663Notes

Reaction equation

HRID 1993663 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([O:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-])=O)=[CH:19][N:18]=2)[CH2:12][CH2:11]1)=[O:9]>[Pd].C(O)C>[NH2:24][C:20]1[CH:21]=[C:22]([CH3:23])[C:17]([O:16][CH:13]2[CH2:14][CH2:15][N:10]([C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[O:9])[CH2:11][CH2:12]2)=[N:18][CH:19]=1

Participants

4

Reactant 1

HCID 68540106HCID 68540106, compound

Product 1

HCID 59134449HCID 59134449, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Stir a mixture of (2-fluoro-phenyl)-[4-(3-methyl-5-nitro-pyridin-2-yloxy)-piperidin-1-yl]-methanone (3.58 g, 10 mmol) and 10% palladium on carbon (358 mg) in ethanol (100 mL) at 22° C. under hydrogen overnight. Filter to remove catalyst. Concentrate filtrate to provide a colorless oil. Subject oil to silica gel chromatography eluting with hexanes and ethyl acetate (1:1), followed by 70% ethyl acetate/hexanes to give a yellow solid (2.27 g, 50% yield). MS(ES): m/z=330.2 [M+H].

Workup

  1. filtrationFilter
  2. customto remove catalyst
  3. customConcentrate filtrate to provide a colorless oil
  4. washeluting with hexanes and ethyl acetate (1:1)

Sources & evidence

ORD record
ord-bd2907ef3a9b45bab3306eeb48421ca8
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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