HCID 178526477, compound → HCID 178507344, compound

HRID 1896770Notes

Reaction equation

HRID 1896770 reaction equation
[N+:1]([C:4]1[CH:19]=[CH:18][C:7]2[NH:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[OH:17])=[N:10][C:6]=2[CH:5]=1)([O-])=O>C(OCC)(=O)C.O.C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:19]=[CH:18][C:7]2[NH:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[OH:17])=[N:10][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 178526477HCID 178526477, compound

Product 1

HCID 178507344HCID 178507344, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 86628739HCID 86628739, compoundSolvent

Procedure

To 2-(5-nitro-1H-benzo[d]imidazol-2-yl)phenol (90 mg, 0.35 mmol) in ethyl acetate/water/acetic acid 1:1:0.01 v/v/v (10 mL) was added palladium on carbon (15 mg). The reaction vessel was purged three times with nitrogen, followed by three times with hydrogen, and then left stirring under hydrogen for 2 h. The reaction vessel was finally purged three times with nitrogen, before filtration on a pad of Celite®, which was washed with ethyl acetate. The organic layer was washed with saturated aqueous NaHCO3. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting with ethyl acetate/hexanes 2:1 v/v to afford 60 mg (76%) of the title compound (LCMS RT=5.39 min, MH+ 226.1)

Workup

  1. customThe reaction vessel was purged three times with nitrogen
  2. waitleft
  3. customThe reaction vessel was finally purged three times with nitrogen
  4. filtrationbefore filtration on a pad of Celite®, which
  5. washwas washed with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous NaHCO3
  7. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  8. customevaporated
  9. customThe resulting solid was purified by column chromatography
  10. washeluting with ethyl acetate/hexanes 2:1 v/v

Sources & evidence

ORD record
ord-a8892d6378f544cd9a13d775caec00ee
Source dataset
uspto-grants-2013_08
Patent number
US08518980B2

Reaction notes

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