Lithium Hydroxide → 6-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 706753Notes

Reaction equation

HRID 706753 reaction equation
[OH-].[Li+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]([O:15]CC)=[O:14])=[CH:11][N:12]=2)[CH:9]=1>C1COCC1.C(O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]([OH:15])=[O:14])=[CH:11][N:12]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 22031055Ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 220319126-Bromoimidazo[1,2-a]pyridine-3-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Lithium hydroxide (0.427 g, 17.8 mmol) was added to a stirred suspension of ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate (2.40 g, 8.92 mmol) in 20 mL of a 4:1 mixture of THF/ethanol. The mixture was stirred under nitrogen for 3 days at ambient temperature. The pH of the mixture was adjusted to neutral (by the addition of aqueous mineral acid) inducing a heavy precipitation of off-white colored solids. The solids were isolated by filtration and dried under reduced pressure to give the desired product (2.0 g; 93%).

Workup

  1. additionby the addition of aqueous mineral acid) inducing
  2. customa heavy precipitation of off-white colored solids
  3. customThe solids were isolated by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-f6f43e3c193448888af51dc97454f1a0
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

Loading…