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Sodium Bicarbonate → N-(4-Bromo-2-methoxy-6-methylphenyl)-7-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-benzimidazol-2-amine

HRID 1698552
Notes
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Reaction equation

HRID 1698552 reaction equation
Cl[C:2]1[N:6]([CH3:7])[C:5]2[C:8]([N:12]3[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]3[CH3:18])=[CH:9][CH:10]=[CH:11][C:4]=2[N:3]=1.[Br:19][C:20]1[CH:26]=[C:25]([CH3:27])[C:23]([NH2:24])=[C:22]([O:28][CH3:29])[CH:21]=1.C(=O)([O-])O.[Na+]>>[Br:19][C:20]1[CH:26]=[C:25]([CH3:27])[C:23]([NH:24][C:2]2[N:6]([CH3:7])[C:5]3[C:8]([N:12]4[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]4[CH3:18])=[CH:9][CH:10]=[CH:11][C:4]=3[N:3]=2)=[C:22]([O:28][CH3:29])[CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 106802184-Bromo-2-methoxy-6-methylanilineHCID 672730232-Chloro-7-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-benzimidazole

Product 1

HCID 58012418N-(4-Bromo-2-methoxy-6-methylphenyl)-7-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-benzimidazol-2-amineYield 35%

Conditions

Temperature
110 °C

Procedure

A mixture of 90 mg (0.347 mmol) of 2-chloro-7-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-benzimidazole and 225 mg (1.04 mmol) of 4-bromo-2-methoxy-6-methylaniline was stirred at 110° C. for 15 hours. After cooling, the reaction mixture was neutralized by saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 60-90% ethylacetate/n-hexane gradient mixture. The desired fractions were collected and evaporated in vacuo, the residual solids were washed with diethyl ether to give 53.4 mg (35%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (X2)
  3. washThe combined organic layer was washed with brine (X1)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a 60-90% ethylacetate/n-hexane gradient mixture
  8. customThe desired fractions were collected
  9. customevaporated in vacuo
  10. washthe residual solids were washed with diethyl ether

Sources & evidence

ORD record
ord-cc32ebf868ba429a95bef9c51efb9729
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163935B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes