Acetic Acid → HCID 68761658, compound

HRID 1878625Notes

Reaction equation

HRID 1878625 reaction equation
C([O:3][C:4](=O)[CH:5]=[CH:6][C:7]1[C:12]([Br:13])=[CH:11][N:10]=[CH:9][C:8]=1[Br:14])C.[BH4-].[Na+].C(O)(=O)C>CCO>[Br:13][C:12]1[CH:11]=[N:10][CH:9]=[C:8]([Br:14])[C:7]=1[CH2:6][CH2:5][CH2:4][OH:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydride2×HCID 68764811HCID 68764811, compound

Product 1

HCID 68761658HCID 68761658, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(3,5-dibromo-pyridin-4-yl)-acrylic acid ethyl ester (1 eq, 17.0 mmol, 5.7 g) in EtOH (100 ml) at −18° C. is added NaBH4 (2 eq, 34.0 mmol, 1.29 g). The cooling bath is removed and the mixture is stirred at r.t. for 1.5 h. Then additional NaBH4 (0.78 eq, 13.2 mmol, 0.5 g) is added and the mixture is heated at 50° C. for 6 h. After cooling to r.t., glacial acetic acid is added, then the mixture is concentrated under reduced pressure. The residue is taken up in EtOAc, and washed with aqueous HCl (1M), sat. aqueous NaHCO3 solution, and sat. aqueous NaCl solution. The organic layer is dried with MgSO4, filtered, and concentrated in vacuo. The crude product is purified using column chromatography (hexane/EtOAc) to give the title compound; [M+H]+=295.

Workup

  1. customThe cooling bath is removed
  2. temperaturethe mixture is heated at 50° C. for 6 h
  3. temperatureAfter cooling to r.t.
  4. concentrationthe mixture is concentrated under reduced pressure
  5. washwashed with aqueous HCl (1M), sat. aqueous NaHCO3 solution, and sat. aqueous NaCl solution
  6. dry with materialThe organic layer is dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product is purified

Sources & evidence

ORD record
ord-aa3d38a0134b4f03b8e120ed719d2ba6
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

Loading…