Water → HCID 69022697, compound

HRID 1865072Notes

Reaction equation

HRID 1865072 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH3:29])[CH:10]=[C:11]([C:27]#[N:28])[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH:25]=[O:26])=[CH:15][CH:14]=1)=[O:7])[CH3:4].O>CO>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH3:29])[CH:10]=[C:11]([C:27]#[N:28])[C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:25][OH:26])=[CH:17][CH:18]=1)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86611443HCID 86611443, compound

Product 1

HCID 69022697HCID 69022697, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium borohydride (0.79 g, 2.1 mmol) to 4-cyano-3-(2′-formyl-biphenyl-4-yl)-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (0.50 g, 1.40 mmol, prepared in example E-23) in methanol at 0° C. with stirring. After 1 hour, allow the reaction mixture to warm to ambient temperature. After 2 hours, pour the reaction mixture into water and extract with ethyl acetate. 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:hexane to provide the title compound. Mass spectrum: EI+=360.2

Workup

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

Sources & evidence

ORD record
ord-3f560b1acca547089bb29f93d8d4951e
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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