tert-butyl 5-amino-3-(4-(benzyloxy)phenyl)-4-cyano-1H-pyrazole-1-carboxylate → tert-butyl 5-amino-4-cyano-3-(4-hydroxyphenyl)-1H-pyrazole-1-carboxylate

HRID 1518288Notes

Reaction equation

HRID 1518288 reaction equation
[NH2:1][C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20]CC3C=CC=CC=3)=[CH:16][CH:15]=2)[C:3]=1[C:28]#[N:29].[H][H]>CCO.[Pd]>[NH2:1][C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:5]=[C:4]([C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)[C:3]=1[C:28]#[N:29]

Participants

5

Reactant 2

HCID 59447506tert-butyl 5-amino-3-(4-(benzyloxy)phenyl)-4-cyano-1H-pyrazole-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 136027725tert-butyl 5-amino-4-cyano-3-(4-hydroxyphenyl)-1H-pyrazole-1-carboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of compound 31E (1.3 g, 3.33 mmol) and Pd/C (0.071 g) in EtOH (15 mL) was hydrogenated with a balloon of hydrogen at rt for 6 hours. The solvent was removed, and residue was purified by flash column chromatography on silica gel eluting with 1:1/hexanes:EtOAc to provide 0.85 g of the desired product 31F: 1H NMR (DMSO-d6): δ 9.88 (s, 1H), 7.67 (d, J=8.9 Hz, 2H), 7.64 (s, 2H), 6.87 (d, J=8.9 Hz, 2H), 1.59 (s, 9H). MS (DCI(+)): m/z 301 (M+H).

Workup

  1. customThe solvent was removed
  2. customresidue was purified by flash column chromatography on silica gel eluting with 1:1/hexanes

Sources & evidence

ORD record
ord-da17435d34b846cd9172a642c0a13cf9
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

Loading…