HCID 14882629, compound → HCID 14882631, compound

HRID 330170Notes

Reaction equation

HRID 330170 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9](/[CH:13]=[C:14](/[C:16](=[O:21])[NH:17][CH2:18][CH2:19][CH3:20])\[CH3:15])=[CH:10][CH:11]=2)[C:6]([CH2:22][C:23]2[CH:41]=[CH:40][C:26]([C:27]([NH:29][S:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[CH3:39])(=[O:32])=[O:31])=[O:28])=[CH:25][C:24]=2[O:42][CH3:43])=[CH:5]1)[CH:2]=[CH2:3]>[Pd].C(O)C>[CH3:43][O:42][C:24]1[CH:25]=[C:26]([CH:40]=[CH:41][C:23]=1[CH2:22][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([CH2:13][CH:14]([C:16](=[O:21])[NH:17][CH2:18][CH2:19][CH3:20])[CH3:15])[CH:8]=2)[N:4]([CH2:1][CH2:2][CH3:3])[CH:5]=1)[C:27]([NH:29][S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH3:39])(=[O:32])=[O:31])=[O:28]

Participants

4

Reactant 1

HCID 14882629HCID 14882629, compound

Product 1

HCID 14882631HCID 14882631, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (10% w/w, 0.1 g) was added to a solution of E-4-[1-allyl-5-[2-(propylcarbamoyl)-1-propenyl]indol-3-ylmethyl]-3-methoxy-N-(2-methylphenylsulfonyl)benzamide (0.24 g) in ethanol (10 ml). The mixture was vigorously stirred and hydrogenated at atmospheric pressure for 4 hr. The catalyst was removed by filtration through diatomaceous earth, the filter pad washed with ethanol, and the filtrate evaporated. The white foam obtained was precipitated from a mixture of ethanol and 1M hydrochloric acid to give the title compound (0.2 g, 82%) as a white powder; mp 104°-110° (softens at 84°).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. washthe filter pad washed with ethanol
  3. customthe filtrate evaporated
  4. customThe white foam obtained
  5. customwas precipitated from a mixture of ethanol and 1M hydrochloric acid

Sources & evidence

ORD record
ord-7cf2b900bb70423f9f1dde3b7bb0120c
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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