Pyridine → HCID 68386507, compound

HRID 1051177Notes

Reaction equation

HRID 1051177 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]([NH:27][CH2:28][CH2:29][C:30]([F:33])([F:32])[F:31])[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>ClCCl.C([O-])(=O)C.C([O-])(=O)C.[Cu+2].O>[Br:17][C:18]1[CH:19]=[C:20]([NH:27][CH2:28][CH2:29][C:30]([F:33])([F:32])[F:31])[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]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 12753Pyridine N-OxideHCID 66691674HCID 66691674, compoundHCID 68386921HCID 68386921, compound

Product 1

HCID 68386507HCID 68386507, compoundYield 22.8%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 751 mg [4-(cyclopropylcarbamoyl)-3-methylphenyl]boronic acid in 68.6 mL dichloromethane were added 528 mg (1.71 mmol) 6-bromo-N-(3,3,3-trifluoropropyl)-1H-benzimidazol-4-amine which was prepared according to intermediate example 1b, 623 mg copper(II)diacetate, 179 mg pyridine 1-oxide and 416 μL pyridine. The mixture was stirred at 23° C. for two days. Water was added and the mixture was extracted with dichloromethane and methanol. The organic layer was washed with water and dried over sodium sulfate. After filtration and removal of the solvent the residue was purified by chromatography to give 188 mg (22%) of the title compound.

Workup

  1. customwas prepared
  2. extractionthe mixture was extracted with dichloromethane and methanol
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and removal of the solvent the residue
  6. customwas purified by chromatography

Sources & evidence

ORD record
ord-2394e83d8cbb448ea14f202cf1470b2d
Source dataset
uspto-grants-2016_07
Patent number
US09388140B2

Reaction notes

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