HCID 66856886, compound → HCID 11524449, compound

HRID 1170858Notes

Reaction equation

HRID 1170858 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]=[C:10]2[CH2:18][CH2:17][CH2:16][C:15]3[N:14]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:13]=[CH:12][C:11]2=3)[CH2:4][CH2:3]1>CCO.[Pd]>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH:10]2[CH2:18][CH2:17][CH2:16][C:15]3[N:14]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:13]=[CH:12][C:11]2=3)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 66856886HCID 66856886, compound

Product 1

HCID 11524449HCID 11524449, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Pd-C (100 mg, 20%) is added to a solution of a mixture of E/Z isomers of 4,5,6,7-tetrahydro-4-(2-(4-methylpiperidin-1-yl)ethylidene)-1-phenyl-1H-indazole (324 mg, 1.01 mmol) in 75 mL of EtOH, and the resulting solution is stirred in a nitrogen atmosphere (45 psi) in a Parr hydrogenator for 18 hours. The reaction mixture is purged with nitrogen, filtered through Celite and the solvent is evaporated under reduced pressure. The resulting crude product is purified by means of silica gel chromatography giving 4,5,6,7-tetrahydro-4-(2-(4-methylpiperidin-1-yl)ethyl)-1-phenyl-1H-indazole (130 mg, 0.40 mmol, 40%, oil).

Workup

  1. customThe reaction mixture is purged with nitrogen
  2. filtrationfiltered through Celite
  3. customthe solvent is evaporated under reduced pressure
  4. customThe resulting crude product is purified by means of silica gel chromatography

Sources & evidence

ORD record
ord-aa22ec0386c8474cbc218c532951ee71
Source dataset
uspto-grants-2010_11
Patent number
US07829559B2

Reaction notes

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