8-(3-Chloro-4-fluorophenyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine → HCID 66604224, compound

HRID 71112Notes

Reaction equation

HRID 71112 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:9]2([CH3:32])[CH2:14][CH2:13][CH2:12][N:11]3[C:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5[O:28][C:27]([CH3:29])=[N:26][CH:25]=5)=[C:20]([O:30][CH3:31])[CH:19]=4)=[N:16][N:17]=[C:10]23)[CH:5]=[CH:6][C:7]=1[F:8]>CO.[OH-].[Pd+2].[OH-]>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2([CH3:32])[CH2:14][CH2:13][CH2:12][N:11]3[C:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5[O:28][C:27]([CH3:29])=[N:26][CH:25]=5)=[C:20]([O:30][CH3:31])[CH:19]=4)=[N:16][N:17]=[C:10]23)=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 666037938-(3-Chloro-4-fluorophenyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 66604224HCID 66604224, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 8-(3-chloro-4-fluorophenyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine (80.0 mg) in methanol (1.8 mL) was added palladium hydroxide (8.0 mg), and the mixture was stirred for 5 days under a hydrogen stream. The catalyst was removed, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (26.0 mg).

Workup

  1. customThe catalyst was removed
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-1a7bb60dff3b44018dbf09891f534e8e
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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