Sodium Bicarbonate → HCID 58536689, compound

HRID 2390865Notes

Reaction equation

HRID 2390865 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10]C(OC)=O)=[N:6][C:7]=1[O:8][CH3:9].C([O-])(O)=[O:16].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][OH:16])=[N:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67001081Methyl 2-(5-bromo-6-methoxypyridin-2-yl)acetate

Product 1

HCID 58536689HCID 58536689, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

step d—A solution of 357c (0.060 g), 5% aq. NaHCO3 (2 mL) and MeOH (2 mL) was heated at reflux for 2 h. The reaction mixture was partitioned between H2O and EtOAc and the combined EtOAc extracts were dried, filtered and evaporated in vacuo. The crude product was purified by SiO2 chromatography eluting with 25% EtOAc/hexane to afford 356a.

Workup

  1. temperatureat reflux for 2 h
  2. customThe reaction mixture was partitioned between H2O and EtOAc
  3. dry with materialthe combined EtOAc extracts were dried
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with 25% EtOAc/hexane

Sources & evidence

ORD record
ord-ce290abab4c543beb991b12de76f2c6c
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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