Sodium Bicarbonate → (5-Bromo-6-methoxypyridin-2-yl)methanol
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
Product 1
Reagents, catalysts & solvents 1
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
- temperatureat reflux for 2 h
- customThe reaction mixture was partitioned between H2O and EtOAc
- dry with materialthe combined EtOAc extracts were dried
- filtrationfiltered
- customevaporated in vacuo
- customThe crude product was purified by SiO2 chromatography
- 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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