2,2'-Bipyridine → HCID 68290206, compound

HRID 878783Notes

Reaction equation

HRID 878783 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11].[CH:14]1(B(O)O)[CH2:16][CH2:15]1.N1C=CC=C[C:21]=1C1C=CC=CN=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCCl>[CH:14]1([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[C:2]2[C:10]([O:12][CH2:13][CH3:21])=[O:11])[CH2:16][CH2:15]1

Participants

8

Reactant 5

HCID 14742,2'-Bipyridine2×HCID 10340Sodium Carbonate3×HCID 25517Ammonium ChlorideHCID 70992Methyl 1H-indole-2-carboxylateHCID 2760897Cyclopropylboronic acid3×

Product 1

HCID 68290206HCID 68290206, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalyst2×HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 1H-indole-2-carboxylate (1.00 g, 5.71 mmol), cyclopropylboronic acid (981 mg, 11.4 mmol), copper (II) acetate (1.04 g, 5.71 mmol), 2,2-bipyridyl (892 mg, 5.71 mmol), sodium carbonate (1.21 g, 11.4 mmol) and 1,2-dichloroethane (15.0 mL) was stirred at 70° C. for 19 hours. Then, thereto were added cyclopropylboronic acid (981 mg, 11.4 mmol) and sodium carbonate (1.21 g, 11.4 mmol), and the mixture was stirred at 70° C. for 8 hours, and then thereto were added cyclopropylboronic acid (981 mg, 11.4 mmol), sodium carbonate (1.21 g, 11.4 mmol), copper (II) acetate (1.04 g, 5.71 mmol) and 2,2-bipyridyl (892 mg, 5.71 mmol), and the mixture was stirred at 70° C. for 16 hours. The mixture was let stand to cool, and then to the reaction mixture was added saturated aqueous ammonium chloride solution. The mixture was filtered through diatomaceous earth, and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→17:3) to give ethyl 1-cyclopropyl-1H-indole-2-carboxylate (882 mg, 72%) as a powder.

Workup

  1. stirringthe mixture was stirred at 70° C. for 8 hours
  2. stirringthe mixture was stirred at 70° C. for 16 hours
  3. temperatureto cool
  4. filtrationThe mixture was filtered through diatomaceous earth
  5. extractionthe filtrate was extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1→17:3)

Sources & evidence

ORD record
ord-0c4564e94d394888885c1689c307b05b
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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