Lithium hydroxide, monohydrate → Lithium 7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxylate

HRID 79301Notes

Reaction equation

HRID 79301 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]3[C:16]([C:19]([O:21]CC)=[O:20])=[CH:17][N:18]=[C:12]3[CH:11]=2)[CH2:3][CH2:2]1.O.[OH-].[Li+:26]>O1CCCC1.O.O1CCCC1>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]3[C:16]([C:19]([O-:21])=[O:20])=[CH:17][N:18]=[C:12]3[CH:11]=2)[CH2:3][CH2:2]1.[Li+:26]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67259084Ethyl 7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 67261208Lithium 7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxylateYield 105.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Ethyl 7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxylate (1 g, 3.13 mmol) was dissolved in tetrahydrofuran/water (4:1, 0.5 M). Lithium hydroxide monohydrate (131 mg, 3.13 mmol) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was diluted with additional tetrahydrofuran and concentrated. Drying under high vacuum for 6 hours gave lithium 7-(2-morpholinoethoxy)imidazo[1,2-a]pyridine-3-carboxylate as a pale yellow solid (979 mg).

Workup

  1. concentrationconcentrated
  2. customDrying under high vacuum for 6 hours

Sources & evidence

ORD record
ord-6baf5a532be44eaf91f713b8e21dc424
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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