Thionyl Chloride → N-(2-bromo-6-methoxy-3-pyridinyl)-2-methylnicotinamide

HRID 1415666Notes

Reaction equation

HRID 1415666 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=O.[K+].S(Cl)(Cl)=O.C(N(C(C)C)CC)(C)C.[NH2:25][C:26]1[C:27]([Br:34])=[N:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1>C(Cl)(Cl)Cl>[Br:34][C:27]1[C:26]([NH:25][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[N:10][C:2]=2[CH3:1])=[CH:31][CH:30]=[C:29]([O:32][CH3:33])[N:28]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531Diisopropylethylamine2×HCID 152093242-Bromo-6-methoxypyridin-3-amineHCID 23677259Potassium 2-methylnicotinate

Product 1

HCID 54100862N-(2-bromo-6-methoxy-3-pyridinyl)-2-methylnicotinamideYield 78.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a suspension of potassium 2-methylnicotinate (1.96 g) in chloroform (30 mL) was added thionyl chloride (2.5 mL). The mixture was stirred overnight at room temperature under a drying tube. Diisopropylethylamine (5 mL) was added followed by 3-amino-2-bromo-6-methoxypyridine (2.25 g). After 10 minutes additional diisopropylethylamine (5 mL) was added. After 2 hours the mixture was diluted with chloroform, washed with water, dried (Na2SO4,) filtered, and evaporated. Chromatography of the residue over silica gel (chloroform/methanol) gave N-(2-bromo-6-methoxy-3-pyridinyl)-2-methylnicotinamide (2.80 g).

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4,)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-96e7e5bad3c14b46a820461038b1ab3b
Source dataset
uspto-grants-1999_06
Patent number
US05908841

Reaction notes

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