HCID 21254087, compound → HCID 57227654, compound

HRID 1531547Notes

Reaction equation

HRID 1531547 reaction equation
[H][H].[CH2:3]([N:10]([CH2:26][CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([N+:37]([O-])=O)[CH:35]=2)[NH:30][C:29]=1[C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([CH3:47])[CH:41]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>[Ni]>[NH2:37][C:34]1[CH:35]=[C:36]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([CH3:47])[CH:41]=1)=[C:28]2[CH2:27][CH2:26][N:10]([CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 21254087HCID 21254087, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57227654HCID 57227654, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a stirred solution of N-{4-[4-(benzyl-{2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]ethyl}amino)butyl]phenyl} methanesulfonamide (491 mg in 30 mL absolute ethanol) was added ca. 30 mg of Raney® nickel. The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 2.5 hours the reaction was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo. Purification by flash chromatography on silica gel (hexane:ethyl acetate, 2:3; then 1:3) gave the title compound (344 mg).

Workup

  1. customevacuated
  2. customAfter 2.5 hours the reaction was flushed with nitrogen
  3. filtrationfiltered over diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-b754f4cdb0844a2b8c8db4999d82755c
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

Loading…