Trifluoroacetic acid → HCID 21249906, compound

HRID 1532371Notes

Reaction equation

HRID 1532371 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=2)[NH:13][C:12]=1[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][CH2:38][CH2:39][CH:40]=O)[CH:32]=1.FC(F)(F)C(O)=O.C([BH3-])#N.[Na+]>CO>[CH2:1]([N:8]([CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=2)[NH:13][C:12]=1[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)[CH2:40][CH2:39][CH2:38][CH2:37][C:33]1[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 110190264-pyridin-3-ylbutanalHCID 21249905HCID 21249905, compound

Product 1

HCID 21249906HCID 21249906, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of benzyl-{2-[2-(3,5-dimethylphenyl)-5-nitro-1H-indol-3-yl]ethyl}amine (700 mg) and 4-pyridin-3-yl butyraldehyde (314 mg) were solvated in 30 mL dry methanol to which ca. 2 g powdered 3 Å molecular sieves were added. The pH of this mixture was adjusted to 5 by the addition of trifluoroacetic acid and then 441 mg sodium cyanoborohydride was added and the mixture atirred at room temperature. After 48 hours, the mixture was filtered through diatomaceous earth, concentrated in vacuo and purified by flash chromatography on silica gel (methylene chloride:methanol:ammonium hydroxide, 96:4:0; then 96:4:1) to give the title compound (676 mg).

Workup

  1. additionwere added
  2. customatirred at room temperature
  3. filtrationthe mixture was filtered through diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography on silica gel (methylene chloride

Sources & evidence

ORD record
ord-dc9f66f7fe9b4c378086a5e05ea9c90d
Source dataset
uspto-grants-2001_03
Patent number
US06200957B1

Reaction notes

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