Water → HCID 66727697, compound

HRID 573279Notes

Reaction equation

HRID 573279 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.[H-].[Na+].Cl[C:12]1[N:16]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:15]2[CH:25]=[CH:26][CH:27]=[CH:28][C:14]=2[N:13]=1.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:12]2[N:16]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:23])([CH3:24])[CH3:22])[C:15]3[CH:25]=[CH:26][CH:27]=[CH:28][C:14]=3[N:13]=2)=[N:6][CH:7]=1.[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([C:12]2[N:16]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:23])([CH3:24])[CH3:22])[C:15]3[CH:25]=[CH:26][CH:27]=[CH:28][C:14]=3[N:13]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 597528982-Chloro-1-[[2-(trimethylsilanyl)ethoxy]methyl]-benzimidazoleHCID 178515818HCID 178515818, compound

Product 2

HCID 66727697HCID 66727697, compoundHCID 66728126HCID 66728126, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 5-bromopyridin-2-ol (500 mg) in DMF (10 mL) was added NaH (60% in oil, 115 mg) at room temperature. The mixture was stirred at room temperature for 30 min and then 2-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzo[d]imidazole (813 mg) was added. The mixture was exposed to microwave irradiation at 200° C. for 1 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/MeOH) and crystallized from AcOEt/hexane to give 2-(5-bromopyridin-2-yloxy)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole (336 mg) and 5-bromo-1-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one (170 mg).

Workup

  1. customirradiation at 200° C. for 1 h
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (AcOEt/MeOH)
  6. customcrystallized from AcOEt/hexane

Sources & evidence

ORD record
ord-e968865c3f5b4a24807d1cb84cf239d5
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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