5-Bromo-2-methoxypyridine → HCID 13433420, compound

HRID 233573Notes

Reaction equation

HRID 233573 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][N:3]=1.[CH3:10][O:11]C1C=CC(Br)=CN=1.C([Li])CCC>O1CCCC1>[CH3:10][O:11][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 27348955-Bromo-2-methoxypyridineHCID 116584942-Bromo-5-(methylthio)pyridineHCID 178418339Butyllithium

Product 1

HCID 13433420HCID 13433420, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

For example, 2-bromo-5-methylthiopyridine may be prepared by the treatment of 2-methoxy-5-bromopyridine (Shiao. M. J. et. al. Syn. Comm. 20(19), 2971, 1990) with n-butyllithium in anhydrous tetrahydrofuran at -78 ° C. followed by quenching the reaction with dimethyldisulfide to afford 2-methoxy-5-methylthiopyridine. Demethylation provides 2-hydroxy-5-methylthiopyridine which upon reaction with phosphorousoxybromide yields the desired 2-bromo-5-methylthiopyridine starting material. (Scheme 7) ##STR19##

Workup

  1. customby quenching
  2. customthe reaction with dimethyldisulfide

Sources & evidence

ORD record
ord-c1393a34c87c413eb89d69d24eafa025
Source dataset
uspto-grants-1997_01
Patent number
US05593994

Reaction notes

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