Pyridine → HCID 68386499, compound

HRID 1051175Notes

Reaction equation

HRID 1051175 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][C:8]=2[CH3:16])=[O:6])[CH2:3][CH2:2]1.[Br:17][C:18]1[CH:19]=[C:20]([NH2:27])[C:21]2[N:25]=[CH:24][NH:23][C:22]=2[CH:26]=1.[N+]1([O-])C=CC=CC=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[NH2:27][C:20]1[C:21]2[N:25]=[CH:24][N:23]([C:10]3[CH:11]=[CH:12][C:7]([C:5]([NH:4][CH:1]4[CH2:3][CH2:2]4)=[O:6])=[C:8]([CH3:16])[CH:9]=3)[C:22]=2[CH:26]=[C:18]([Br:17])[CH:19]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 12753Pyridine N-OxideHCID 66691674HCID 66691674, compoundHCID 683865391360899-50-8

Product 1

HCID 68386499HCID 68386499, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [4-(cyclopropylcarbamoyl)-3-methylphenyl]boronic acid (13.95 g, 63.68 mmol) in DCM (160 mL) at rt was added under a nitrogen atmosphere 6-bromo-1H-benzimidazol-4-amine (6.75 g, 31.84 mmol), copper(II)acetate (11.57 g, 63.68 mmol), pyridine N-oxide (3.33 g, 35.02 mmol) and pyridine (7.55 g, 95.53 mmol). After stirring overnight at rt, the mixture was stirred at 40° C. for 3 days. Filtration through ALLOX, extraction with water and evaporation of the organic phase gave the crude product, which was purified by flash chromatography to yield 6 g 4-(4-amino-6-bromo-1H-benzimidazol-1-yl)-N-cyclopropyl-2-methylbenzamide (50%).

Workup

  1. stirringthe mixture was stirred at 40° C. for 3 days
  2. filtrationFiltration
  3. extractionthrough ALLOX, extraction
  4. customwith water and evaporation of the organic phase
  5. customgave the crude product, which
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-f6a9a790c4d54fbf88fb8e5de64e4d0f
Source dataset
uspto-grants-2016_07
Patent number
US09388140B2

Reaction notes

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