Hydrochloric Acid → 7-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid

HRID 1748190Notes

Reaction equation

HRID 1748190 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([O:13]CC)=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.[OH-].[Na+].Cl>CO>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([OH:13])=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67260906Ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 672614887-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate (67 g, 250 mmol) in methanol (500 mL), sodium hydroxide (2N, 249 ml, 500 mmol) was added. The resulting solution was stirred overnight at room temperature. The pH of the solution was adjusted to pH=6 with HCl (2N). The solids were collected by filtration to afford 7-bromo-imidazo[1,2-a]pyridine-3-carboxylic acid as white solid. MS [M+H]+ 241/243. 1H-NMR: (DMSO-d6, 300 MHz): 13.3 (br, 1H), 9.19 (dd, J=7.5, 0.9 Hz, 1H), 8.25 (s, 1H), 8.15 (d, J=1.5 Hz, 1H), 7.39 (dd, J=7.5, 1.8 Hz, 1H).

Workup

  1. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-27eb0d7943bb41e8b221885ca14bd813
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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