Sulfuric acid magnesium salt (1:1) → HCID 9849603, compound

HRID 1956537Notes

Reaction equation

HRID 1956537 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH2:20])=[CH:15][C:14]([C:21]2[N:25]=[C:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[O:23][N:22]=2)=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.S([O-])([O-])(=O)=O.[Mg+2].[N:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH2:42][CH2:43][CH2:44][CH:45]=O)[CH:37]=1.[BH4-].[Na+]>>[CH3:8][C:6]1[CH:5]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH:20][CH2:45][CH2:44][CH2:43][CH2:42][C:38]2[CH:37]=[N:36][CH:41]=[CH:40][CH:39]=2)=[CH:15][C:14]([C:21]2[N:25]=[C:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[O:23][N:22]=2)=[CH:13][CH:12]=3)[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 110190264-pyridin-3-ylbutanalHCID 21249884HCID 21249884, compound

Product 1

HCID 9849603HCID 9849603, compoundYield 89.7%

Procedure

To a solution of 2-[2-(3,5-dimethylphenyl)-5-(5-isobutyl-[1,2,4]oxadiazol-3-yl)-1H-indol-3-yl]ethylamine (22 mg in 1.5 mL chloroform) at 0° C. was added anhydrous magnesium sulfate (38 nrg) followed by 4-(3-pyridyl)-butanal (11 mg) and the mixture stirred at low temperature for 15 minutes. At this time sodium borohydride (3.7 mg in 0.50 mL methanol) was added and the mixture stirred at 0° C. After 30 minutes, the reaction was quenched by the addition of water and the mixture extracted with ethyl acetate The organic portion was washed successively with saturated potassium carbonate and brine then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride: methanol, 92:8) gave the title compound (26.5 mg). m/e=522 (M+H)

Workup

  1. stirringthe mixture stirred at 0° C
  2. waitAfter 30 minutes
  3. customthe reaction was quenched by the addition of water
  4. extractionthe mixture extracted with ethyl acetate The organic portion
  5. washwas washed successively with saturated potassium carbonate and brine
  6. dry with materialthen dried over sodium sulfate
  7. customPurification of the
  8. concentrationconcentrate by flash chromatography on silica gel (methylene chloride: methanol, 92:8)

Sources & evidence

ORD record
ord-fd1df0517c9243b0bc5db2e2682f5b8c
Source dataset
uspto-grants-1998_07
Patent number
US05780437

Reaction notes

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