Benzophenone imine → 1-[5-(benzhydrylidene-amino)-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one

HRID 896331Notes

Reaction equation

HRID 896331 reaction equation
Br[C:2]1[CH:29]=[CH:28][C:5]2[N:6]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:7]([CH2:9][N:10]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[N:12]([CH:19]([CH3:21])[CH3:20])[C:11]3=[O:22])=[N:8][C:4]=2[CH:3]=1.[C:30](=[NH:43])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:30](=[N:43][C:2]1[CH:29]=[CH:28][C:5]2[N:6]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:7]([CH2:9][N:10]3[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[N:12]([CH:19]([CH3:21])[CH3:20])[C:11]3=[O:22])=[N:8][C:4]=2[CH:3]=1)([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

8

Reactant 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 208139981-[5-bromo-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-oneHCID 23676156Sodium t-butoxide

Product 1

HCID 865901151-[5-(benzhydrylidene-amino)-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-oneYield 87%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-[5-bromo-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one (45 mg, 0.1 mmol), benzophenone imine (22 mg, 0.12 mmol), sodium tert-butoxide (13 mg, 0.14 mmol), BINAP (19 mg, 0.03 mmol) and Pd2(dba)3 (9 mg, 0.01 mmol) in toluene (2 mL) was heated to reflux for 6 h. After cooling, the reaction mixture was diluted with EtOAc and washed with sat. NaHCO3 and brine. The organic layer was dried over MgSO4 and evaporated. The residue was purified by flash chromatography (hexanes:EtOAc 4:1 to 1:1) to give 48 mg (87%) of 1-[5-(benzhydrylidene-amino)-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h
  3. temperatureAfter cooling
  4. washwashed with sat. NaHCO3 and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography (hexanes:EtOAc 4:1 to 1:1)

Sources & evidence

ORD record
ord-e1b7b152ff3d4ba49f062d31991d1cce
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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