HCID 21254087, compound → HCID 57227654, compound

HRID 1292398Notes

Reaction equation

HRID 1292398 reaction equation
[CH2:1]([N:8]([CH2:24][CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([N+:35]([O-])=O)[CH:33]=2)[NH:28][C:27]=1[C:38]1[CH:43]=[C:42]([CH3:44])[CH:41]=[C:40]([CH3:45])[CH:39]=1)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Ni]>[NH2:35][C:32]1[CH:33]=[C:34]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27]([C:38]1[CH:43]=[C:42]([CH3:44])[CH:41]=[C:40]([CH3:45])[CH:39]=1)=[C:26]2[CH2:25][CH2:24][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 21254087HCID 21254087, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57227654HCID 57227654, compoundYield 74.8%

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 (59 mg in 4 mL absolute ethanol) was added ca. 15 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 3 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, 1:2) gave the title compound (42 mg).

Workup

  1. customevacuated
  2. customAfter 3 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:ethyl acetate, 1:2)

Sources & evidence

ORD record
ord-e5019786db7c466cbc0e8c874fc66ae7
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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