Cesium carbonate → HCID 178492558, compound

HRID 547621Notes

Reaction equation

HRID 547621 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[C:12]3[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:11]=3[N:10]=[CH:9]2)C=CC=CC=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)N2C3C=C(O)C=CC=3N=C2)C=CC=CC=1.F[C:60]1[CH:67]=[CH:66][C:63]([CH:64]=[O:65])=[CH:62][C:61]=1[O:68][CH3:69].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[NH:8]1[C:12]2[CH:13]=[CH:14][C:15]([O:17][C:60]3[CH:67]=[CH:66][C:63]([CH:64]=[O:65])=[CH:62][C:61]=3[O:68][CH3:69])=[CH:16][C:11]=2[N:10]=[CH:9]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27373584-Fluoro-3-methoxybenzaldehydeHCID 57585916HCID 57585916, compoundHCID 67197432HCID 67197432, compound

Product 1

HCID 178492558HCID 178492558, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(triphenylmethyl)-1H-benzimidazol-5-ol and 1-(triphenylmethyl)-1H-benzimidazol-6-ol (750 mg, 2.0 mmol), 4-fluoro-3-(methyloxy)benzaldehyde (461 mg, 3.0 mmol) and cesium carbonate (972 mg, 3.0 mmol) were heated in dimethylformamide at 80 degrees centigrade for 2 hours. The reaction was diluted with water and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over MgSO4, concentrated and dried under vacuum for approximately 18 hours. The residue was dissolved in 15 mL of tetrahydrofuran and stirred with 5 mL or 4N HCl in dioxane for 4 days. The reaction was concentrated and purified by preparative HPLC. Pure fractions were diluted with 1N NaOH to make basic and then extracted twice with ethyl acetate. The organic layers were dried over MgSO4 and concentrated to give 4-(1H-benzimidazol-5-yloxy)-3-(methyloxy)benzaldehyde. (M+1) 269.0, 1.34 min (LC/MS method B)

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customdried under vacuum for approximately 18 hours
  6. dissolutionThe residue was dissolved in 15 mL of tetrahydrofuran
  7. concentrationThe reaction was concentrated
  8. custompurified by preparative HPLC
  9. additionPure fractions were diluted with 1N NaOH
  10. extractionextracted twice with ethyl acetate
  11. dry with materialThe organic layers were dried over MgSO4
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-89b273eb3dba4fa195ed72bd4d6e6560
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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