Hexane → t-Butyl 4-[4-(4-amino-2-fluorophenoxy)pyridin-2-ylcarbamoyl]piperidine-1-carboxylate

HRID 492680Notes

Reaction equation

HRID 492680 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[O:13])[CH:6]=1.CCCCCC.C(OCC)(=O)C>CO.[C].[Pd]>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:12]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:16][CH2:15]3)=[O:13])[CH:6]=2)=[C:2]([F:1])[CH:30]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 8857Ethyl Acetate2×HCID 23153115t-Butyl 4-[4-(2-fluoro-4-nitrophenoxy)pyridin-2-ylcarbamoyl]piperidine-1-carboxylate

Product 1

HCID 23153131t-Butyl 4-[4-(4-amino-2-fluorophenoxy)pyridin-2-ylcarbamoyl]piperidine-1-carboxylateYield 36.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 887MethanolSolvent2×

Procedure

To a solution of a crude product of t-butyl 4-[4-(2-fluoro-4-nitrophenoxy)pyridin-2-ylcarbamoyl]piperidine-1-carboxylate (548 mg) in methanol (50 ml) was added 10% palladium carbon (100 mg), followed by stirring under a hydrogen atmosphere at room temperature for 2 hrs. The catalyst was filtered. The filtrate was concentrated under a reduced pressure to give a residue, which was then subjected to silica gel column chromatography (Fuji Silysia BW-300, eluent; hexane:ethyl acetate=1:1 to 1:2, then ethyl acetate) to provide a mixture of the starting material and the target compound. The mixture was dissolved in methanol (50 ml) again, and then 10% palladium carbon (100 mg) was added thereto, followed by stirring under a hydrogen atmosphere at room temperature for 2 hrs. The catalyst was filtered. The filtrate was concentrated under a reduced pressure to give a residue, which was then filtered by silica gel. The filtrate was concentrate under a reduced pressure to provide the titled compound (185 mg) as a yellow oil.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationThe filtrate was concentrated under a reduced pressure
  3. customto give a residue, which
  4. additiona mixture of the starting material
  5. stirringby stirring under a hydrogen atmosphere at room temperature for 2 hrs
  6. filtrationThe catalyst was filtered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customto give a residue, which
  9. filtrationwas then filtered by silica gel
  10. concentrationThe filtrate was concentrate under a reduced pressure

Sources & evidence

ORD record
ord-1d1c4a1de6b144d5a8e52685a9030d42
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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