Sulfuric acid magnesium salt (1:1) → HCID 53793030, compound

HRID 1458371Notes

Reaction equation

HRID 1458371 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=1)=[C:9]2[CH2:23][CH2:24][NH2:25])=[O:5])[CH3:2].S([O-])([O-])(=O)=O.[Mg+2].[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][CH2:39][CH2:40][CH:41]=O)[CH:33]=1.[BH4-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([C:15]1[CH:16]=[C:17]([Cl:22])[CH:18]=[C:19]([Cl:21])[CH:20]=1)=[C:9]2[CH2:23][CH2:24][NH:25][CH2:41][CH2:40][CH2:39][CH2:38][C:34]1[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 110190264-pyridin-3-ylbutanalHCID 53828516HCID 53828516, compound

Product 1

HCID 53793030HCID 53793030, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3-(2-aminoethyl)-2-(3,5-dichlorophenyl)-1H-indole-5-carboxylic acid ethyl ester (prepared essentially as described in Example 5.1, 100 mg in 7.0 mL chloroform) at -5° C. was added 172 mg of magnesium sulfate followed by 46.3 mg of 4-pyridin-3-yl-butyraldehyde and the mixture stirred at low temperature for 15 minutes. At this time, a solution of sodium borohydride (13.7 mg in 1.2 mL dry methanol) was added and after another 40 minutes, the reaction was quenched by the addition of water. The mixture was partitioned between ethyl acetate and saturated potassium carbonate, extracted and the organic portion washed with brine and dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol, 92:8) gave the title compound (100 mg).

Workup

  1. customat -5° C.
  2. customthe reaction was quenched by the addition of water
  3. customThe mixture was partitioned between ethyl acetate and saturated potassium carbonate
  4. extractionextracted
  5. washthe organic portion washed with brine
  6. dry with materialdried 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-b9d34392535347cf92287f81d9ecdcd5
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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