Lithium Hydroxide → HCID 86717941, compound

HRID 1844180Notes

Reaction equation

HRID 1844180 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:13]([C:17]([O:19]CC)=[O:18])=[C:14]([CH3:16])[N:15]=2)[CH:9]=[CH:10][C:11]=1[F:12].[OH-].[Li+]>C1COCC1.C(O)C>[F:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:13]([C:17]([OH:19])=[O:18])=[C:14]([CH3:16])[N:15]=2)[CH:9]=[CH:10][C:11]=1[F:12]

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 86717940HCID 86717940, compound

Product 1

HCID 86717941HCID 86717941, compound

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

365 mg (0.76 mmol; purity about 76%) of ethyl 8-[(2,6-difluorobenzyl)oxy]-7-fluoro-2-methylimidazo[1,2-a]pyridine-3-carboxylate Example 111A were dissolved in 16.6 ml of THF/ethanol (5:1), 1.14 ml (1.14 mmol) of 1 N aqueous lithium hydroxide solution were added and the mixture was stirred at RT overnight. Another 2.67 ml (2.67 mmol) of 1 N aqueous lithium hydroxide solution were added, and the mixture was stirred at RT overnight. The mixture was concentrated and the aqueous phase was acidified to pH 4 using 6 N hydrochloric acid. A precipitate formed, and the suspension was cooled with ice water. The solid was filtered off and dried under high vacuum. This gave 236 mg of the target compound (87% of theory, purity 94%).

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. concentrationThe mixture was concentrated
  3. customA precipitate formed
  4. filtrationThe solid was filtered off
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-0eac1e888b5c45cfbd332e85962451a5
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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