HCID 15296097, compound → HCID 15296098, compound

HRID 1648134Notes

Reaction equation

HRID 1648134 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2([CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:9]2)=[CH:3][CH:2]=1>C(O)C.[Pd]>[C:17]1([CH:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([CH2:23][C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)([CH2:7][C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH2:9]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 15296097HCID 15296097, compound

Product 1

HCID 15296098HCID 15296098, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1,1-bis(4-pyridinylmethyl)-3-phenyl-1H-indene (5.8 g, 15.5 nmol ) in 95% ethanol (100 ml), was added 5% palladium on carbon catalyst (1.45 g) and the mixture was shaken under hydrogen (50 psig) at room temperature for 2 h. The catalyst was removed by filtration, and the solvent removed by rotary evaporation. The oil was purified via column chromatography (silica gel, 10% methanol/dichloromethane) to give pure 4-((2,3-dihydro-3-phenyl-1-(4-pyridinylmethyl)-1H-inden-l-ylmethyl))-pyridine. NMR (200 MHz, CDCl3) δ 2.05 (dd, 1H); 2.38 (dd, 1H); 2.93 (dd, 2H); 3.15 (dd, 2H); 3.42 (m, 1H); 6.67 (dd, 4H); 7.00 (d, 2H); 7.10-7.34 (m, 7H); 8.36 (d, 2H, J=5 Hz); 8.42 (d, 2H, J=5 Hz). Mass Calcd. for C27H24N2 : 376.1937. Found: 376.1951.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent removed by rotary evaporation
  3. customThe oil was purified via column chromatography (silica gel, 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-d9f0f29f042d46918f159aeb71f20609
Source dataset
uspto-grants-1995_07
Patent number
US05434264

Reaction notes

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