Hydrochloric Acid → 8-[(2,6-Difluorobenzyl)oxy]-6-ethynyl-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid
Reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:14]([C:18]([O:20]CC)=[O:19])=[C:15]([CH3:17])[N:16]=2)[CH:9]=[C:10]([C:12]#[CH:13])[CH:11]=1.[OH-].[Li+].Cl>O1CCCC1.CO>[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:14]([C:18]([OH:20])=[O:19])=[C:15]([CH3:17])[N:16]=2)[CH:9]=[C:10]([C:12]#[CH:13])[CH:11]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
580 mg of ethyl 8-[(2,6-difluorobenzyl)oxy]-6-ethynyl-2-methylimidazo[1,2-a]pyridine-3-carboxylate (Example 38A; contained 35% of the methyl ester) were initially charged in 30 ml of tetrahydrofuran and 5 ml of methanol, and 7.8 ml of 1N aqueous lithium hydroxide solution were added. The resulting reaction mixture was stirred at room temperature for 6 h and then kept at 0° C. for 16 h. The mixture was then acidified with 6 N hydrochloric acid and concentrated. The solid which formed was filtered off, triturated with a little water and filtered off again. Drying under reduced pressure gave 521 mg of the desired product (quantitative yield).
Workup
- customThe resulting reaction mixture
- waitkept at 0° C. for 16 h
- concentrationconcentrated
- customThe solid which formed
- filtrationwas filtered off
- customtriturated with a little water
- filtrationfiltered off again
- customDrying under reduced pressure
Sources & evidence
- ORD record
- ord-1f351636e76a4de3adb02f2016197a31
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946215B2
Reaction notes
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