2,2'-Bipyridine → HCID 90308949, compound

HRID 2283668Notes

Reaction equation

HRID 2283668 reaction equation
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].N1C=CC=CC=1C1C=CC=CN=1.[N+:24]([C:27]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:28]=1[CH:29]=[CH:30][NH:31]2)([O-:26])=[O:25]>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:1]1([N:31]2[C:32]3[C:28](=[C:27]([N+:24]([O-:26])=[O:25])[CH:35]=[CH:34][CH:33]=3)[CH:29]=[CH:30]2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 14742,2'-BipyridineHCID 1457664-Nitro-1H-indoleHCID 516892Sodium BicarbonateHCID 2760897Cyclopropylboronic acid

Product 1

HCID 90308949HCID 90308949, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 111,2-DichloroethaneSolvent

Procedure

Cyclopropyl boronic acid (1.0 g), sodium bicarbonate (0.99 g), copper acetate (II) (1.1 g), and 2,2′-bipyridine (0.92 g) were added to a solution of 4-nitro-1H-indole (0.96 g) in 1,2-dichloroethane (60 ml). The reaction solution was stirred at room temperature for 7 days, and then further stirred at 60° C. for 2 hours. The insolubles were filtrated through celite, and then the resultant was washed successively with water and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 1-cyclopropyl-4-nitro-1H-indole as a yellow solid.

Workup

  1. stirringfurther stirred at 60° C. for 2 hours
  2. filtrationThe insolubles were filtrated through celite
  3. washthe resultant was washed successively with water
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was evaporated under vacuum
  6. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4e148fae70dd465e84a0759e97bef852
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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