Sulfuric acid magnesium salt (1:1) → {2-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]propyl}-(4-pyridin-4-yl-butyl)amine

HRID 1458370Notes

Reaction equation

HRID 1458370 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][CH:10]=O)=[CH:3][CH:2]=1.[CH3:12][C:13]1[CH:14]=[C:15]([C:20]2[NH:21][C:22]3[C:27]([C:28]=2[CH:29]([CH3:32])[CH2:30][NH2:31])=[CH:26][C:25]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:24][CH:23]=3)[CH:16]=[C:17]([CH3:19])[CH:18]=1.S([O-])([O-])(=O)=O.[Mg+2].[BH4-].[Na+]>>[CH3:19][C:17]1[CH:16]=[C:15]([C:20]2[NH:21][C:22]3[C:27]([C:28]=2[CH:29]([CH3:32])[CH2:30][NH:31][CH2:10][CH2:9][CH2:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:26][C:25]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:24][CH:23]=3)[CH:14]=[C:13]([CH3:12])[CH:18]=1

Participants

5

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 114464344-Pyridin-4-ylbutanalHCID 221009152-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]propylamine

Product 1

HCID 22100895{2-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]propyl}-(4-pyridin-4-yl-butyl)amineYield 42.2%

Conditions

Temperature
-5 °C

Procedure

A mixture of 4-pyridin-4-yl-butyraldehyde (23 mg), 2-[2-(3,5-dimethylphenyl)-5-methanesulfonyl-1H-indol-3-yl]propylamine (50 mg) and magnesium sulfate (76 mg) were diluted with 1.5 mL CDCl3 and stirred at -5° C. After 15 minutes, a solution of sodium borohydride (6.8 mg in 1.5 mL dry methanol) were added and the mixture stirred at low temperature for an additional 20 minutes. At this time the reaction was quenched by the addition of water, extracted with ethyl acetate and the organic portion washed sequentially with water and brine then dried over sodium sulfate. Purification of the concentrate by preparative TLC on silica gel (methylene chloride:methanol, 9:1) gave the title compound (29 mg).

Workup

  1. additionwere diluted with 1.5 mL CDCl3
  2. stirringthe mixture stirred at low temperature for an additional 20 minutes
  3. customAt this time the reaction was quenched by the addition of water
  4. extractionextracted with ethyl acetate
  5. washthe organic portion washed sequentially with water and brine
  6. dry with materialthen dried over sodium sulfate
  7. customPurification of the
  8. concentrationconcentrate by preparative TLC on silica gel (methylene chloride:methanol, 9:1)

Sources & evidence

ORD record
ord-0d3758a6a3f04a7d89192f9dedee5088
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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