Acetic Acid → HCID 178419327, compound

HRID 1512171Notes

Reaction equation

HRID 1512171 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)/[CH:10]=[CH:11]/[CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:4]([N+:19]([O-])=O)[CH:3]=1.C(O)(=O)C>CO.[Fe]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9](/[CH:10]=[CH:11]/[CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:19][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67528902(E)-N-(4-Bromo-2-nitro-phenyl)-3-(tetrahydro-pyran-4-yl)-acrylamide

Product 1

HCID 178419327HCID 178419327, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

A solution of (E)-N-(4-bromo-2-nitro-phenyl)-3-(tetrahydro-pyran-4-yl)-acrylamide (1.26 g, 3.55 mmol, as prepared in the previous step) in 25 mL anhydrous MeOH was treated with glacial acetic acid (4 mL) and Fe powder (0.991 g, 0.0177 mol) and heated to 85° C. under a reflux condenser for 2 h. The resulting mixture was concentrated in vacuo, treated with saturated aqueous NaHCO3 (200 mL) and extracted thrice with 125 mL CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was triturated with CH2Cl2, and the resulting solid was filtered and air-dried. The mother liquor was purified on an 80-g Sepra Si 50 SPE column (Isco system: flow rate=30 mL/min; eluting with EtOAc/hexane, 40:60 v/v over 10 min and 40:60 to 100:0, v/v over 30 min to yield (E)-5-bromo-2-[2-(tetrahydro-pyran-4-yl)-vinyl]-1H-benzimidazole as a white solid.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. additiontreated with saturated aqueous NaHCO3 (200 mL)
  3. extractionextracted thrice with 125 mL CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with CH2Cl2
  7. filtrationthe resulting solid was filtered
  8. customair-dried
  9. customThe mother liquor was purified on an 80-g Sepra Si 50 SPE column (Isco system
  10. washeluting with EtOAc/hexane, 40:60 v/v over 10 min

Sources & evidence

ORD record
ord-605f2ba532bc489aa99cb0b37fa80e57
Source dataset
uspto-grants-2012_07
Patent number
US08217060B2

Reaction notes

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