Sodium borohydride → HCID 10048445, compound

HRID 275355Notes

Reaction equation

HRID 275355 reaction equation
[I-].[CH3:2][C:3]1[N:4]([C:20]2[CH:25]=[CH:24][N+:23]([CH2:26][CH2:27][N:28]3[CH2:32][CH2:31][NH:30][C:29]3=[O:33])=[CH:22][CH:21]=2)[C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=[CH:9][C:8]([CH3:19])=[CH:7][CH:6]=2.[BH4-].[Na+]>C(O)C>[CH3:2][C:3]1[N:4]([C:20]2[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][N:28]3[CH2:32][CH2:31][NH:30][C:29]3=[O:33])[CH2:22][CH:21]=2)[C:5]2[C:10]([C:11]=1[C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)=[CH:9][C:8]([CH3:19])=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10076392HCID 10076392, compound

Product 1

HCID 10048445HCID 10048445, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[2,5-Dimethyl-3-(4-fluorophenyl)-1H-indol-1-yl]-1-[2-(imidazolidin-2-on-1-yl)ethyl]-pyridinium iodide 5a (6.3 g) was suspended in ethanol (100 ml) and sodium borohydride (2.1 g) was added in three portions during 3.5 h. Then the solvent was evaporated in vacuo and water (100 ml) was added. The mixture obtained was extracted with dichloromethane (2×50 ml). The combined organic phases were washed with brine (100 ml) and dried (MgSO4). Evaporation of the solvent gave the title compound as an oil, which was purified by column chromatography on silica gel (eluted with ethyl acetate/ethanol 8:1 containing 4% triethylamine). Yield: 2.5 g, mp 151°-153° C.

Workup

  1. customThen the solvent was evaporated in vacuo and water (100 ml)
  2. additionwas added
  3. customThe mixture obtained
  4. extractionwas extracted with dichloromethane (2×50 ml)
  5. washThe combined organic phases were washed with brine (100 ml)
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-38e941ede7af4b928270206260a0fedc
Source dataset
uspto-grants-1995_02
Patent number
US05393761

Reaction notes

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