Triethylamine → 3-Formyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine

HRID 1195729Notes

Reaction equation

HRID 1195729 reaction equation
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([OH:12])[C:6]2=[N:5][C:4]=1[CH3:13])=[O:2].C(N([CH2:19][CH3:20])CC)C>CO.O>[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][C@@H:10]3[C:19]4[C:20](=[CH:1][CH:3]=[CH:4][CH:13]=4)[CH2:6][C@H:11]3[OH:12])[C:6]2=[N:5][C:4]=1[CH3:13])=[O:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 232941873-Formyl-8-hydroxy-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 228438253-Formyl-8-(2-(trans)-hydroxy-2,3-dihydro-1-indenyloxy)-2-methyl-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

12 g (68 mmol) of 3-formyl-8-hydroxy-2-methyl-imidazo[1,2-a]pyridine, 18 g (136 mmol) of 1,2-indenoxide and 9,6 ml (68 mmol) of triethylamine are stirred in 95 ml methanol/water (4:1) for 14 hours at 40° C. The mixture is evaporated at 50° C. in the rotary evaporator, mixed with 200 ml icewater, rendered alkaline with sodium hydroxide solution (approximately pH 13), and the precipitate is filtered off. The filtrate is shaken out with dichloromethane and the organic phase made up to 250 ml with dichloromethane, combined with the precipitate, dried with magnesium sulfate and purified with active charcoal. 250 ml of toluene is added, dichloromethane is distilled off, the mixture is purified at the boiling point with bleaching earth (e.g. Tonsil®), evaporated to half its volume and allowed to crystallize in the refrigerator. The yield of the titel compound m.p. 200°-202° C. is 17.6 g (84%).

Workup

  1. customThe mixture is evaporated at 50° C. in the rotary evaporator
  2. additionmixed with 200 ml icewater
  3. filtrationis filtered off
  4. dry with materialdried with magnesium sulfate
  5. custompurified with active charcoal
  6. addition250 ml of toluene is added
  7. distillationdichloromethane is distilled off
  8. customthe mixture is purified at the boiling point with bleaching earth (e.g. Tonsil®)
  9. customevaporated to half its volume
  10. customto crystallize in the refrigerator

Sources & evidence

ORD record
ord-401bd105063e4879a1a972bc10b5ee89
Source dataset
uspto-grants-1992_05
Patent number
US05112834

Reaction notes

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