HCID 70069091, compound → HCID 18971778, compound

HRID 2395406Notes

Reaction equation

HRID 2395406 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]4[C:31]5[CH:30]=[CH:29][N:28]=[CH:27][C:26]=5[N:25]=[C:24]4[CH3:32])=[CH:19][CH:18]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1>O1CCCC1.CO.[Pd]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]4[C:31]5[CH:30]=[CH:29][N:28]=[CH:27][C:26]=5[N:25]=[C:24]4[CH3:32])=[CH:19][CH:18]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 70069091HCID 70069091, compound

Product 1

HCID 18971778HCID 18971778, compoundYield 76.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A cis and trans mixture of 1-[4-[2-[3-(cyclopentyloxy)-4-methoxyphenyl]-ethenyl]phenyl]-2-methyl-1H-imidazo[4,5-c]pyridine (300 mg, 0.705 mmol 1.0 eq) and 300 mg of 10% Pd/C in 10 ml of tetrahydrofuran and 10 ml of methanol was placed on a Parr hydrogenation apparatus and shaken under 50 psi H2 at room temperature for 6 hours. The reaction mixture was filtered through celite, concentrated, and chromatographed on a silica gel column eluting with 5% CH3OH-CH2Cl2 to give 230 mg of clear oil. Recrystallization from ether-hexane gave 239 mg, 79%, of white crystals. M.P.: 123°-125° C. Elemental Analysis Calc'd for C27 H28N3O2 : Calc'd: C, 75.85; H, 6.84; N, 9.83. Found: C, 75.83; H, 6.74; N, 9.65.

Workup

  1. filtrationThe reaction mixture was filtered through celite,
  2. concentrationconcentrated
  3. customchromatographed on a silica gel column
  4. washeluting with 5% CH3OH-CH2Cl2

Sources & evidence

ORD record
ord-e21595cc7c1744baae9223b618cb18c5
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

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