Acetic Acid → HCID 59620012, compound

HRID 445711Notes

Reaction equation

HRID 445711 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:10]=[C:11]([CH3:13])[CH3:12])[C:5]([CH2:8][CH3:9])=[N:6][CH:7]=1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][CH:11]([CH3:12])[CH3:13])[C:5]([CH2:8][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 59619684HCID 59619684, compound

Product 1

HCID 59620012HCID 59620012, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To solution of (5-bromo-2-ethyl-pyridin-3-yl)-isopropylidene-amine (Stage 162.1.2, 1.17 mmol) in dichloromethane (25 ml) was added AcOH (0.25 ml) and sodium triacetoxyborohydride (3.51 mmol). The reaction mixture was stirred for 4 h at rt. The RM was quenched with aqueous NaHCO3 and extracted with dichloromethane (2×). The combined organic layers were washed with saturated aqueous NaHCO3, with brine, dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and eluted (CH2Cl2/MeOH 0% to 3%). The fractions containing the product were purified by preparative HPLC. The fractions containing pure product were basified with NaHCO3, concentrated and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered and evaporated to the title compound as an oil (HPLC: tR 2.40 min (Method A); M+H=243, 245 MS-ES).

Workup

  1. customThe RM was quenched with aqueous NaHCO3
  2. extractionextracted with dichloromethane (2×)
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3, with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was absorbed on silica gel
  8. washeluted (CH2Cl2/MeOH 0% to 3%)
  9. additionThe fractions containing the product
  10. customwere purified by preparative HPLC
  11. additionThe fractions containing pure product
  12. concentrationconcentrated
  13. extractionextracted with EtOAc (3×)
  14. dry with materialThe combined organic layers were dried over Na2SO4
  15. filtrationfiltered
  16. customevaporated to the title compound as an oil (HPLC: tR 2.40 min (Method A); M+H=243, 245 MS-ES)

Sources & evidence

ORD record
ord-5116eb56056c4cfc955c755c531988c4
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

Loading…