HCID 15523805, compound → Ethyl 3-[(1S)-2-amino-1-methylethyl]-2-(3,5-dimethylphenyl)-α,α-dimethyl-1H-indole-5-acetate

HRID 850669Notes

Reaction equation

HRID 850669 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]([C:8]1[CH:9]=[C:10]2[C:14](=[C:15](Br)[CH:16]=1)[NH:13][C:12]([C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[CH:19]=1)=[C:11]2[C@H:26]([CH3:29])[CH2:27][NH2:28])([CH3:7])[CH3:6])[CH3:2].[H][H]>[Pd]>[CH2:1]([O:3][C:4](=[O:30])[C:5]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:18]1[CH:19]=[C:20]([CH3:25])[CH:21]=[C:22]([CH3:24])[CH:23]=1)=[C:11]2[C@H:26]([CH3:29])[CH2:27][NH2:28])([CH3:7])[CH3:6])[CH3:2]

Participants

4

Reactant 2

HCID 15523805HCID 15523805, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15523806Ethyl 3-[(1S)-2-amino-1-methylethyl]-2-(3,5-dimethylphenyl)-α,α-dimethyl-1H-indole-5-acetateYield 103.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of (S)-2-[3-(2-amino-1-methylethyl)-7-bromo-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid ethyl ester (79 mg in 1 mL methanol) was added 8 mg of 10% palladium on carbon catalyst. The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 7 hours the reaction was flushed with nitrogen, filtered over diatomaceous earth, concentrated in vacuo and purified by flash chromatography on silica gel (chloroform:methanol, 92:8) to provide the title compound (68 mg).

Workup

  1. customevacuated
  2. customAfter 7 hours the reaction was flushed with nitrogen
  3. filtrationfiltered over diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography on silica gel (chloroform:methanol, 92:8)

Sources & evidence

ORD record
ord-00900c4bcfd04ad2bb5fc0d8f3dcbcd2
Source dataset
uspto-grants-2000_01
Patent number
US06017944

Reaction notes

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