Water → tert-Butyl 3-(tert-butoxycarbonylphenylmethyl)-5-cyano-2-oxo-2,3-dihydro-benzimidazole-1-carboxylate

HRID 1631957Notes

Reaction equation

HRID 1631957 reaction equation
[C:1]([O:5][C:6]([CH:8]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[N:9]1[C:13]2[CH:14]=[C:15](I)[CH:16]=[CH:17][C:12]=2[N:11]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]1=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[CH3:34][N:35](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6]([CH:8]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[N:9]1[C:13]2[CH:14]=[C:15]([C:34]#[N:35])[CH:16]=[CH:17][C:12]=2[N:11]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:10]1=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 66754745Tert-butyl 3-(tert-butoxycarbonylphenylmethyl)-5-iodo-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

Product 1

HCID 66755109tert-Butyl 3-(tert-butoxycarbonylphenylmethyl)-5-cyano-2-oxo-2,3-dihydro-benzimidazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

1.74 (3.16 mmol) of tert-butyl 3-(tert-butoxycarbonylphenylmethyl)-5-iodo-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (XIIb) were dissolved in 20 ml of dry DMF and stirred under a stream of nitrogen for 20 min. 482 mg (4.11 mmol) of zinc(II) cyanide and 292 mmol (0.25 mmol) of Pd[P(Ph)3]4 were added, and the reaction solution was stirred at 80° C. for 1.5 h. The cooled reaction solution was mixed with 70 ml of water and extracted with ethyl acetate (3×). The combined organic phases were washed with saturated NaCl solution and dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was purified by chromatography on silica gel (mobile phase gradient 10-30% ethyl acetate in cyclohexane). Yield: 1.08 g (76%) of white solid

Workup

  1. stirringthe reaction solution was stirred at 80° C. for 1.5 h
  2. customThe cooled reaction solution
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic phases were washed with saturated NaCl solution
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by chromatography on silica gel (mobile phase gradient 10-30% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-cb1450c8b4a5414ca9f99bb14b8f0e49
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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