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

HRID 2284621Notes

Reaction equation

HRID 2284621 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6](C(C#N)=[CH:9][N:10]=2)[CH:7]=1.[OH-:13].[Na+].[CH3:15][CH2:16][OH:17]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:15]([C:16]([OH:13])=[O:17])=[CH:9][N:10]=2)[CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 220310786-Bromoimidazo[1,2-a]pyridine-3-carbonitrile

Product 1

HCID 220319126-Bromoimidazo[1,2-a]pyridine-3-carboxylic acid

Procedure

A stirring solution of 6-bromoimidazo[1,2-a]pyridine-3-carbonitrile [JMC 54(7). 2455-2466; 2011] (1.0 g), EtOH (10 mL) and aq. NaOH (1.0 g, 10 mL) was heated at 100° C. After 12 h, the reaction mixture was cooled and concentrated to dryness by rotary evaporator under reduced pressure. Subsequently, the crude solid was diluted with water, cooled in ice-bath and acidified with conc. HCl till pH 4 while stirring. The resulting suspension was suction filtered and the solid was dried overnight. Subsequently, the collected solid was further dried over P2O5 under high vacuum to obtain 6-bromoimidazo[1,2-a]pyridine-3-carboxylic acid (0.91 g) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 13.27 (s, 1H), 9.36 (s, 1H), 8.24 (s, 1H), 7.77 (d, J=9.5 Hz, 1H), 7.67 (d, J=9.5, 1.7 Hz, 1H).

Workup

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated to dryness by rotary evaporator under reduced pressure
  3. additionSubsequently, the crude solid was diluted with water
  4. temperaturecooled in ice-bath
  5. filtrationsuction filtered
  6. customthe solid was dried overnight
  7. dry with materialSubsequently, the collected solid was further dried over P2O5 under high vacuum

Sources & evidence

ORD record
ord-49c582a52d92480c9f0ddab960fdbe08
Source dataset
uspto-grants-2015_09
Patent number
US09145433B2

Reaction notes

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