2-Methylpyridine → HCID 178419667, compound

HRID 473443Notes

Reaction equation

HRID 473443 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].[Li]C.[Br-:10].[Mg+2:11].[Br-]>C1COCC1>[Br:10][Mg:11][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

5

Reactant 3

HCID 79752-MethylpyridineHCID 82241Magnesium BromideHCID 178418348HCID 178418348, compound

Product 1

HCID 178419667HCID 178419667, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of picoline (31.9 mL, 1.5 eq) in THF (300 mL) was added MeLi (202 mL, 1.6 M, 1.5 eq) drop-wise at −40° C. under nitrogen. The reaction mixture was allowed to warm to −20° C. and stirred for 10 min. and then cooled to −40° C. and magnesium bromide (59.4 g, 1.5 eq) was added in three portions. The reaction mixture was allowed to warm to rt, stirred for 30 min to provide bromo(pyridin-2-ylmethyl)magnesium.

Workup

  1. temperaturecooled to −40° C.
  2. temperatureto warm to rt
  3. stirringstirred for 30 min

Sources & evidence

ORD record
ord-f6864e5db01d48fbb3b5dcf40a967565
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

Loading…