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Triethylamine → 8-(trans-2,3-Dihydro-2-hydroxy-1-indenyloxy)-6-methoxymethyl-2,3-dimethyl-imidazo[1,2-a]pyridine

HRID 2053041
Notes
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Reaction equation

HRID 2053041 reaction equation
[OH:1][C:2]1[C:3]2[N:4]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:5]=[C:6]([CH2:8][O:9][CH3:10])[CH:7]=1.[O:16]1[CH:18]2[CH2:19][C:20]3[C:25]([CH:17]12)=[CH:24][CH:23]=[CH:22][CH:21]=3.C(N(CC)CC)C.[Cl-].[NH4+]>CO.O>[OH:16][C@@H:18]1[CH2:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@H:17]1[O:1][C:2]1[C:3]2[N:4]([C:11]([CH3:15])=[C:12]([CH3:14])[N:13]=2)[CH:5]=[C:6]([CH2:8][O:9][CH3:10])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 92838Indene oxideHCID 692875158-Hydroxy-6-methoxymethyl-2,3-dimethyl-imidazo[1,2-a]pyridine

Product 1

HCID 691142778-(trans-2,3-Dihydro-2-hydroxy-1-indenyloxy)-6-methoxymethyl-2,3-dimethyl-imidazo[1,2-a]pyridineYield 45%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 1.0 g (4.9 mmol) 8-hydroxy-6-methoxymethyl-2,3-dimethyl-imidazo[1,2-a]pyridine and 1.3 g (9.7 mmol) 1,2-epoxyindane in 12 ml methanol and 3 ml water are added 1.4 ml triethylamine and the mixture is heated to 50° C. for 24 h. After cooling down, the reaction mixture is poured into 100 ml saturated aqueous ammonium chloride and extracted with dichloromethane. The organic phase is dried over anhydrous magnesium sulphate and evaporated. Purification of the residue by column chromatography on silica gel using dichloromethane:methanol (20:1) yields 0.7 g (45%) of the title compound as a colourless solid (m.p. 142-143° C.).

Workup

  1. temperatureAfter cooling down
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase is dried over anhydrous magnesium sulphate
  4. customevaporated
  5. customPurification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-4d04100cd3e3490c9035f70b725cb50f
Source dataset
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07326718B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes