2,2'-Bipyridine → HCID 86703246, compound

HRID 2204425Notes

Reaction equation

HRID 2204425 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]1.[CH:10]1(B(O)O)[CH2:12][CH2:11]1.N1C=CC=CC=1C1C=CC=CN=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:10]1([N:1]2[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[CH:2]2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 14742,2'-BipyridineHCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 12361759methyl 1H-pyrrole-3-carboxylate

Product 1

HCID 86703246HCID 86703246, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 1H-pyrrole-3-carboxylate (500 mg, 4.00 mmol), cyclopropylboronic acid (686 mg, 7.99 mmol), copper(II) acetate (726 mg, 4.00 mmol), 2,2′-bipyridyl (624 mg, 4.00 mmol), sodium carbonate (847 mg, 7.99 mmol) was stirred at 70° C. for 16 hr, concentrated, diluted in EtOAc/water, and extracted twice with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated. The crude material was purified by silica gel column chromatography (hexane/EtOAc 4:1) to afford the title compound (377 mg, 57% yield) as a yellow oil. TLC (hexane/EtOAc 4:1): Rf=0.26.

Workup

  1. concentrationconcentrated
  2. additiondiluted in EtOAc/water
  3. extractionextracted twice with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel column chromatography (hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-4c7e14684c724464a6b260b1f0257719
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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