tert-butyl 4-(4-{6-[(E)-2-(dimethylamino)ethenyl]-5-nitropyridin-3-yl}-1H-pyrazol-1-yl)piperidine-1-carboxylate → tert-butyl 4-[4-(1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

HRID 1404608Notes

Reaction equation

HRID 1404608 reaction equation
C[N:2](C)/[CH:3]=[CH:4]/[C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][N:14]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[CH:15]=2)=[CH:7][C:6]=1[N+]([O-])=O>CO.[Pd]>[NH:2]1[C:6]2[C:5](=[N:10][CH:9]=[C:8]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[CH2:18][CH2:17]4)[CH:15]=3)[CH:7]=2)[CH:4]=[CH:3]1

Participants

4

Reactant 1

HCID 58532279tert-butyl 4-(4-{6-[(E)-2-(dimethylamino)ethenyl]-5-nitropyridin-3-yl}-1H-pyrazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 58532272tert-butyl 4-[4-(1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylateYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(4-{6-[(E)-2-(dimethylamino)ethenyl]-5-nitropyridin-3-yl}-1H-pyrazol-1-yl)piperidine-1-carboxylate (prepared in example 18: 4.0 g, 9.05 mmol) in MeOH (50 mL) was added Pd—C (10%, wet, 2.0 g) and the reaction mixture was hydrogenated under a hydrogen balloon at room temperature for 2 h. The catalyst was filtered off and solvent was evaporated. The residue was washed with ethyl acetate to give a solid (3.1 g, yield 93%).

Workup

  1. customat room temperature
  2. customfor 2 h
  3. filtrationThe catalyst was filtered off
  4. customsolvent was evaporated
  5. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-2e5f758575e64b78a04a44cb6fafed2c
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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