Hydrochloric Acid → 7-(Trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 405783Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]([O-:14])=[O:13])=[CH:10][N:11]=[C:5]2[CH:4]=1.[Li+].[OH-].Cl>C1COCC1.CO>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]([OH:14])=[O:13])=[CH:10][N:11]=[C:5]2[CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirring solution of ethyl 7-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylate (23) (100 mg, 0.387 mmol) in THF:MeOH (4:1, 1.5 mL) was added 2N LiOH (0.25 mL). The reaction was heated at 60° C. for 1 hour. Then, cooled to room temperature and the pH was adjusted between 4-5 with 1N HCl. The solvent was partially concentrated and the resulting aqueous layer was lyophilized to give 7-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (24). 1H NMR (400 MHz, d6-DMSO) δ 9.44 (d, J=7.2 Hz, 1H), 8.40 (s, 1H), 8.31-8.30 (m, 1H), 7.48 (dd, J=2.0, 7.6 Hz, 1H). MS m/z 231.2 (M+1)+.

Workup

temperatureThen, cooled to room temperature
concentrationThe solvent was partially concentrated

Sources & evidence

ORD record: ord-f784496733094d62bc1c3696b175fd6b
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754071B2

Reaction notes

Loading…