Sodium borohydride → HCID 18940865, compound

HRID 355994Notes

Reaction equation

HRID 355994 reaction equation
[BH4-].[Na+].[Br-].[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][C:16]1[CH:17]=[N+:18]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[CH:19]=[CH:20][CH:21]=1>CO>[CH3:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][C:16]1[CH2:17][N:18]([CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=2)[CH2:19][CH2:20][CH:21]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18940878HCID 18940878, compound

Product 1

HCID 18940865HCID 18940865, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride in pellets (0.8 g; 0.0211 mol) was added to a cold (~0° C.) stirring mixture of compound of Description 7 [3-[(5-methoxy-1H-indol-3-yl)-methyl]-1-(2-(4-nitro-phenyl)-ethyl)-pyridinium bromide] (1.75 g; 0.0038 mol) in methanol (50 ml). The reaction mixture was stirred at 0° C. for 2 hours. The reaction was then quenched with a saturated solution of aqueous sodium carbonate and the solvent (methanol) was evaporated under vacuum. The product was extracted with methylene chloride. The organic extract was dried (MgSO4) and evaporated under vacuum giving the desired compound (1.38 g). The compound was used as such without further purification.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 2 hours
  2. customThe reaction was then quenched with a saturated solution of aqueous sodium carbonate
  3. customthe solvent (methanol) was evaporated under vacuum
  4. extractionThe product was extracted with methylene chloride
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-eafe3606050c4a57b1749c8a82d84e10
Source dataset
uspto-grants-1998_11
Patent number
US05834493

Reaction notes

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