Lithium Hydroxide → 6-((2,2,2-Trifluoroethoxy)methyl)imidazo[1,2-a]pyridine-3-carboxylic acid

HRID 570337Notes

Reaction equation

HRID 570337 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]([O:17]CC)=[O:16])=[CH:13][N:14]=2)[CH:11]=1.[Li+].[OH-]>C1COCC1.CO.O>[F:21][C:2]([F:1])([F:20])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]2[N:10]([C:12]([C:15]([OH:17])=[O:16])=[CH:13][N:14]=2)[CH:11]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 71280508Ethyl 6-((2,2,2-trifluoroethoxy)methyl)imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 712808426-((2,2,2-Trifluoroethoxy)methyl)imidazo[1,2-a]pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of ethyl 6-((2,2,2-trifluoroethoxy)methyl)imidazo[1,2-a]pyridine-3-carboxylate (97) (280 mg, 0.92 mmol) in THF/MeOH/H2O (3:2:1, 5 mL) was treated with 6N LiOH (0.92 mL, 5.52 mmol) and stirred at room temperature for 1 hour. All solvents were removed and 6N HCl was added to adjust pH 5-6. Then the mixture was purified by HPLC to give 6-((2,2,2-trifluoroethoxy)methyl)imidazo[1,2-a]pyridine-3-carboxylic acid (98). 1H NMR (400 MHz, d6-DMSO) δ 9.34 (m, 1H), 8.40 (s, 1H), 7.88 (dd, J=0.8, 9.2 Hz, 1H), 7.65 (dd, J=1.6, 9.2 Hz, 1H), 4.83 (s, 2H), 4.18 (q, J=9.6 Hz, 2H). MS m/z 275.1 (M+1)+.

Workup

  1. customAll solvents were removed
  2. addition6N HCl was added
  3. customThen the mixture was purified by HPLC

Sources & evidence

ORD record
ord-c487f43e247443d1bc3fa95c4e732d85
Source dataset
uspto-grants-2015_05
Patent number
US09023839B2

Reaction notes

Loading…