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Tetrahydrofuran → HCID 86704973, compound

HRID 572164
Notes
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Reaction equation

HRID 572164 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH2:9][CH2:8][CH2:7][CH:6]([C:10]3[CH:33]=[CH:32][C:13]([O:14][C:15]4[N:19](COCC[Si](C)(C)C)[C:18]5[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=5[N:16]=4)=[CH:12][CH:11]=3)[C:5]=12.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.C1COCC1>O>[N:1]1[CH:2]=[CH:3][N:4]2[CH2:9][CH2:8][CH2:7][CH:6]([C:10]3[CH:11]=[CH:12][C:13]([O:14][C:15]4[NH:19][C:18]5[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=5[N:16]=4)=[CH:32][CH:33]=3)[C:5]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11078149TBAF tetrahydrofuranHCID 86704972HCID 86704972, compound

Product 1

HCID 86704973HCID 86704973, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2-[4-(5,6,7,8-Tetrahydroimidazo[1,2-a]pyridin-8-yl)phenoxy]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazole (0.19 g), 1.0 M tetrabutylammonium fluoride-THF solution (1.7 ml) and THF (3 ml) were stirred under microwave irradiation at 100° C. for 3 hr. The reaction mixture was stirred at 80° C. overnight, poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate) and recrystallized from methanol/ethyl acetate to give the title compound (0.071 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate)
  6. customrecrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-d3613158a148466b8434f1327a7e07b4
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029388B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes