Ethyl Acetate → HCID 18400143, compound

HRID 1019086Notes

Reaction equation

HRID 1019086 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-])=O)=[C:16]([CH3:17])[C:11]=2[N:10]=[C:9]1[CH3:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]2[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:9]([CH3:21])=[N:10][C:11]=2[C:16]=1[CH3:17]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2723923Ammonium formateHCID 18400135HCID 18400135, compound

Product 1

HCID 18400143HCID 18400143, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-t-butoxycarbonyl-2,4-dimethyl-5-nitrobenzimidazole (1.26 g, 4.32 mmol) in methanol (15 mL)/ethyl acetate (100 mL) are added 10% palladium-on-carbon (0.1 g) and ammonium formate (1.09 g, 17.3 mmol). The mixture is stirred at room temperature for 3 hours, then filtered on Celite with a methanol wash of the solids. The filtrate is rotary evaporated and the residue is purified by flash chromatography on silica gel, eluting with 20% ethyl acetate in hexane to afford 5-amino-1-t-butoxycarbonyl-2,4-dimethylbenzimidazole as a white solid.

Workup

  1. filtrationfiltered on Celite with a methanol
  2. washwash of the solids
  3. customThe filtrate is rotary evaporated
  4. customthe residue is purified by flash chromatography on silica gel
  5. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5b82508f81f747988d0ce7d65c19263d
Source dataset
uspto-grants-2002_11
Patent number
US06486190B1

Reaction notes

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