HCID 22477296, compound → HCID 22477299, compound

HRID 549070Notes

Reaction equation

HRID 549070 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C:14]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[CH:21]=[C:20]3[C:27]2[N:35]([S:36]([C:39]3[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=3)(=[O:38])=[O:37])[C:30]3=[N:31][CH:32]=[CH:33][CH:34]=[C:29]3[CH:28]=2)=[CH:13][CH2:12]1)=O)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[N:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[CH:21]=[C:20]3[C:27]2[N:35]([S:36]([C:39]3[CH:40]=[CH:41][C:42]([CH3:45])=[CH:43][CH:44]=3)(=[O:37])=[O:38])[C:30]3=[N:31][CH:32]=[CH:33][CH:34]=[C:29]3[CH:28]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 22477296HCID 22477296, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22477299HCID 22477299, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A mixture of 2-[5-(1-benzyloxycarbonyl-1,2,5,6-tetrahydropyridin-4-yl)-1-methyl-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.7 g, Reference Example 61) ethanol (53 mL) and palladium on carbon (0.35 g) was stirred in the presence of hydrogen for 4 hours, then left standing at room temperature overnight. After a further day a further quantity of palladium on carbon (0.18 g, 10%) was added and stirring was continued in the presence of hydrogen for a further 8 hours. After standing at room temperature for 4 days the reaction mixture was filtered through Hyflo and the filter pad was washed well with ethanol. The combined filtrate and washings was treated with palladium on carbon (0.35 g) and the mixture was stirred in the presence of hydrogen. The mixture was filtered through Hyflo and the filter pad was washed well with ethanol. The combined filtrate and washings was evaporated and the residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (4:1, v/v) to give the title compound as a light brown solid, m.p. 82-85° C.

Workup

  1. waitleft
  2. waitAfter standing at room temperature for 4 days
  3. filtrationthe reaction mixture was filtered through Hyflo
  4. washthe filter pad was washed well with ethanol
  5. additionThe combined filtrate and washings was treated with palladium on carbon (0.35 g)
  6. stirringthe mixture was stirred in the presence of hydrogen
  7. filtrationThe mixture was filtered through Hyflo
  8. washthe filter pad was washed well with ethanol
  9. customThe combined filtrate and washings was evaporated
  10. additionthe residue was subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and pentane (4:1

Sources & evidence

ORD record
ord-7ef8d702796c473fb407c93a9ff6e986
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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