Hydrochloric Acid → 8-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 1784564Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:10]2[CH:11]=[C:12]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[CH:13]=[C:14]([C:15]([F:18])([F:17])[F:16])[C:9]2=[N:8][CH:7]=1)=[O:5])C.O[Li].O.Cl.[Na+].[Cl-]>C1COCC1.CO.O>[F:18][C:15]([F:16])([F:17])[C:14]1[C:9]2[N:10]([C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]=2)[CH:11]=[C:12]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[CH:13]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of the above 8-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester (3.06 g, 7.61 mmol) in THF (45 mL), MeOH (5 mL) and water (11.3 mL) at 23° C. was added LiOH·H2O (479 mg, 11.41 mmol) and the mixture was stirred at 23° C. for 3 h. Poured into icewater, adjusted pH with 1 N HCl (about 11.41 mL) to pH 2-3, saturated with solid NaCl, extracted with EtOAc, dried over Na2SO4. Removal of the solvent in vacuum left the title compound as a light brown solid (2.87 g, 101%). MS (ISN) 373 [(M−H)−]; mp 248° C. (dec.).

Workup

additionPoured into icewater
extractionextracted with EtOAc
dry with materialdried over Na2SO4
customRemoval of the solvent in vacuum
waitleft the title compound as a light brown solid (2.87 g, 101%)

Sources & evidence

ORD record: ord-474b2de1ed724182b0c59b6204071766
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504404B2

Reaction notes

Loading…