Benzaldehyde → HCID 69024560, compound

HRID 1865082Notes

Reaction equation

HRID 1865082 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:22])[C:8]([CH2:20][CH3:21])=[C:9]([C:18]#[N:19])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)=[O:5])[CH3:2].[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[BH4-].[Na+].O>C(O)(=O)C.CO>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:22])[C:8]([CH2:20][CH3:21])=[C:9]([C:18]#[N:19])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([NH:17][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 4311764Sodium borohydrideHCID 69019889HCID 69019889, compound

Product 1

HCID 69024560HCID 69024560, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

Add 3-(4-amino-phenyl)-4-cyano-5-ethyl-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (0.297 g, 1.0 mmol, prepared in example E-153), benzaldehyde (0.106 g, 1.0 mmol), and one drop of acetic acid in methanol with stirring at room temperature. After 4 hours, add sodium borohydride (0.075 g, 2.0 mmol) portionwise and continue stirring at room temperature. After 18 hours, pour the reaction mixture into water and extract with EtOAc. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with ethyl acetate:hexanes to provide the title compound. Mass spectrum (m/e): 388.1 (M+1).

Workup

  1. stirringcontinue stirring at room temperature
  2. waitAfter 18 hours
  3. extractionextract with EtOAc
  4. washwash with water and brine
  5. dry with materialdry over anhydrous magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue by flash chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-1a0739b6629f4b37b8033196b851962d
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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