Pyridine → HCID 86632444, compound

HRID 552920Notes

Reaction equation

HRID 552920 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13](=[O:14])[CH2:12][CH:11]([OH:15])[C:10]2=[O:16])=[CH:4][CH:3]=1.N1C=CC=CC=1.[Br:23][CH2:24][C:25](Br)=[O:26]>ClCCl>[Br:23][CH2:24][C:25]([O:15][CH:11]1[CH2:12][C:13](=[O:14])[N:9]([CH2:8][C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:10]1=[O:16])=[O:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 86632448HCID 86632448, compound

Product 1

HCID 86632444HCID 86632444, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.34 g (5.56 mmol) of 1-[(6-chloropyridin-3-yl)methyl]-3-hydroxypyrrolidin-2,5-dione (XI-1a) and 674 μl (8.34 mmol) of pyridine are dissolved in 15 ml of dichloromethane, and 1.12 g (5.56 mmol) of bromoacetyl bromide are added at 0° C. The mixture is stirred at room temperature for 30 minutes, and ice-water is then added. The organic is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture dichloromethane:methanol (97:3) gives 1.44 g (55% of theory) of 1-[(6-chloropyridin-3-yl)methyl]-2,5-dioxopyrrolidin-3-yl bromoacetate.

Workup

  1. washThe organic is washed successively with saturated sodium bicarbonate solution and saturated sodium chloride solution
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-5b500cc585f14007bf761a7eb964f743
Source dataset
uspto-grants-2011_05
Patent number
US07951951B2

Reaction notes

Loading…