Methanol → 3-Bromo-5-methoxypyridine

HRID 365801Notes

Reaction equation

HRID 365801 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](Br)[CH:7]=1.[H-].[Na+].[CH3:11][OH:12]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([O:12][CH3:11])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 693693,5-Dibromopyridine

Product 1

HCID 8171633-Bromo-5-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 12 g of 3,5-dibromopyridine and 40 g of 60% NaH in DMF was added 4.05 mL of MeOH, and the reaction mixture was stirred for 4 hours at room temperature and 1 hour at 60° C. The DMF was removed under reduced pressure, and the residue was taken directly to the next step. MS (CI/NH3) m/z 188/190 (M+H)+, 205/207 (M+NH4)+. 1H NMR (CDCl3, 300 MHz) δ: 8.32 (d, J=1.8 Hz, 1H), 8.27 (d, J=2.6 Hz, 1H), 7.42 (dd, J=1.8, 2.6 Hz, 1H), 3.88 (s, 3H).

Workup

  1. customThe DMF was removed under reduced pressure

Sources & evidence

ORD record
ord-31b33363742b4d858cb8db092846756d
Source dataset
uspto-grants-2000_10
Patent number
US06127386

Reaction notes

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