Pyridine → HCID 71533616, compound

HRID 2274951Notes

Reaction equation

HRID 2274951 reaction equation
F[C:2](F)(F)[C:3](O)=[O:4].[F:8][C:9]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:10]=1[CH2:11][N:12]1[C:20]2[CH2:19][CH:18]([CH3:21])[NH:17][CH2:16][C:15]=2[C:14]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[N:13]1.C(OC(=O)C)(=O)C.N1C=CC=CC=1>O>[F:8][C:9]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:10]=1[CH2:11][N:12]1[C:20]2[CH2:19][CH:18]([CH3:21])[N:17]([C:3](=[O:4])[CH3:2])[CH2:16][C:15]=2[C:14]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)=[N:13]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 131733417HCID 131733417, compound

Product 1

HCID 71533616HCID 71533616, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1-(2,4-Difluoro-benzyl)-3-(4-fluoro-phenyl)-6-methyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine (7a) (0.53 g, 1.35 mmol), acetic anhydride (5.5 ml) and pyridine (5.5 ml) was stirred at 25° C. for 16 h. The mixture was poured on 50 ml water, extracted with 150 ml ethyl acetate, the combined organic layers were washed with 3 times 0.5 N NaOH (50 ml) and once with brine, dried over MgSO4, filtrated and evaporated to dryness. The crude product was silica gel chromatography (eluting with heptane/ethyl acetate) to give 156 mg of 1-[1-(2,4-Difluoro-benzyl)-3-(4-fluoro-phenyl)-6-methyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl]-ethanone (8z).

Workup

  1. extractionextracted with 150 ml ethyl acetate
  2. washthe combined organic layers were washed with 3 times 0.5 N NaOH (50 ml) and once with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltrated
  5. customevaporated to dryness
  6. washsilica gel chromatography (eluting with heptane/ethyl acetate)

Sources & evidence

ORD record
ord-af267c581b84488eb110857f7f647a95
Source dataset
uspto-grants-2015_09
Patent number
US09127001B2

Reaction notes

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