Chlorosuccinimide → HCID 59589432, compound

HRID 630154Notes

Reaction equation

HRID 630154 reaction equation
[N:1]1[C:2]([CH2:10][OH:11])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[Cl:12]N1C(=O)CCC1=O>CN(C=O)C>[Cl:12][C:3]1[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1][C:2]=1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 2795540Imidazo[1,2-a]pyridin-2-ylmethanol

Product 1

HCID 59589432HCID 59589432, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of imidazo[1,2-a]pyridin-2-ylmethanol (1.0 g, 6.75 mmol) in anhydrous DMF was added 1-chloropyrrolidine-2,5-dione (0.898 g, 6.75 mmol) at room temperature. The reaction mixture was allowed to stir for 2 hours. The solvent was evaporated, and the residue was purified by CombiFlash using dichloromethane and methanol (0-10%) to provide {3-chloroimidazo[1,2-a]pyridin-2-yl}methanol as a grey solid (0.799 g, 65% yield); M+1 183.2.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by CombiFlash

Sources & evidence

ORD record
ord-67a991a188044d558d43804b867f5175
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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