HCID 77221560, compound → HCID 22663243, compound

HRID 380406Notes

Reaction equation

HRID 380406 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:18][C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)[CH:15]=3)[C:10]([CH3:31])=[CH:9]2)=[CH:5][CH:4]=1>O1CCCC1.CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH:17]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:18][C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)[CH:15]=3)[C:10]([CH3:31])=[CH:9]2)=[CH:32][CH:33]=1

Participants

5

Reactant 1

HCID 77221560HCID 77221560, compound

Product 1

HCID 22663243HCID 22663243, compoundYield 18.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of cis- and trans-[1-(4-methoxybenzyl)-3-methyl-6-(1-phenyl-2-pyridin-4-yl-vinyl)-1H-indole (70 mg, Example 22) in a mixture of tetrahydrofuran and methanol (20 ml; 1:1, v/v) was heated at 45-50° C. under an atmosphere of hydrogen in the presence of 6% palladium on activated charcoal then stirred overnight at room temperature. The mixture was filtered through celite then evaporated. The residue was subjected to high pressure liquid chromatography using a hypersilC18 BDS column (250×20 ml, 8 micron) and eluting with methanol containing 0.1% ammonium hydroxide to yield the title compound (13 mg) as an oil. NMR (CDCl3): δ 2.30(s,3H); 3.30-3.40(m,2H); 3.70(s,3H); 4.30-4.40(m,1H); 5.10(s,2H); 6.80-7.50(m,13H); 8.30-8.35(m,2H); 8.50(bs,2H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customthen evaporated
  3. washeluting with methanol containing 0.1% ammonium hydroxide

Sources & evidence

ORD record
ord-469d6838d18940d08f05e7d232a31dd8
Source dataset
uspto-grants-2001_10
Patent number
US06303600B1

Reaction notes

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