2,2'-Bipyridine → HCID 86714649, compound

HRID 1409387Notes

Reaction equation

HRID 1409387 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1.C([O-])([O-])=O.[Na+].[Na+].[CH:16]1(B(O)O)[CH2:18][CH2:17]1.C1C=CN=C(C2C=CC=CN=2)C=1.C([O-])(O)=O.[Na+]>ClC(Cl)C.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH:16]1([N:1]2[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]2)[CH2:18][CH2:17]1

Participants

8

Reactant 5

HCID 14742,2'-BipyridineHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 2760897Cyclopropylboronic acidHCID 178498454HCID 178498454, compound

Product 1

HCID 86714649HCID 86714649, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 63651,1-DichloroethaneSolvent2×

Conditions

Temperature
70 °C

Procedure

Methyl 1H-pyrazole-3-carboxylate (4 g, 31.7 mmol) was dissolved in dichloroethane (160 ml). Na2CO3 (6.72 g, 63.4 mmol) and cyclopropylboronic acid (5.44 g, 63.4 mmol) were added to the solution. The resulting mixture was heated to 70° C. and a hot solution of bipyridine (4.92 g, 31.6 mmol) and Cu(OAc)2 (5.72 g, 31.6 mmol) in dichloroethane (40 ml) was added. The mixture was stirred at 70° C. under an oxygen atmosphere overnight. Saturated aqueous solution of NaHCO3 was added to the reaction mixture and extracted with EtOAc. The organic layer was evaporated and the residue was purified by flash chromatography. Yield 2.5 g. 1H-NMR (400 MHz; DMSO-d6): δ 1.04-1.09 (m, 2H), 1.17-1.23 (m, 2H), 3.64-3.69 (m, 1H), 3.91 (s, 3H), 6.78 (d, 1H), 7.46 (d, 1H).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was evaporated
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-c2bafb8902624610bfd9c18922d8886d
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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