4-Bromoanisole → 7-[(4-Methoxyphenyl)amino]-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 2235547Notes

Reaction equation

HRID 2235547 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CC(C)([O-])C.[Na+].Br[C:45]1[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=1>C1COCC1.C(OCC)(=O)C>[CH3:52][O:51][C:48]1[CH:49]=[CH:50][C:45]([NH:1][C:2]2[C:7]3[N:8]([CH3:12])[C:9](=[O:11])[NH:10][C:6]=3[CH:5]=[CH:4][CH:3]=2)=[CH:46][CH:47]=1

Participants

7

Reactant 4

HCID 77304-BromoanisoleHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 596354197-Amino-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one

Product 1

HCID 685813907-[(4-Methoxyphenyl)amino]-1-methyl-1,3-dihydro-2H-benzimidazol-2-oneYield 42%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 0.183 g (1.12 mmol) of 7-amino-1-methyl-1,3-dihydrobenzimidazol-2-one, 0.037 g (0.11 mmol) of biphenyl-2-yl-dicyclohexylphosphane, 0.237 g (2.47 mmol) of sodium tert-butoxide and 0.041 g (0.045 mmol) of tris(dibenzylidineacetone)dipalladium in 6 mL of THF was treated with 0.14 mL (1.12 mmol) of 4-bromoanisole and heated to 60° C. for 18 h. The crude reaction mixture was diluted with ethyl acetate, filtered through a pad of celite and purified by flash chromatography eluting with a 97% dichloromethane/methanol mixture to give 0.126 g (42%) of the title compound as a tan powder.

Workup

  1. customThe crude reaction mixture
  2. filtrationfiltered through a pad of celite
  3. custompurified by flash chromatography
  4. washeluting with a 97% dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-0940320e366840bbb14d023c91fa7bd7
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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