2,2'-Bipyridine → HCID 86677491, compound

HRID 1621154Notes

Reaction equation

HRID 1621154 reaction equation
C(OC([N:8]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:9][CH2:10][C:11]1[NH:15][N:14]=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:12]=1)=O)(C)(C)C.[CH:29]1(B(O)O)[CH2:31][CH2:30]1.C(=O)([O-])[O-].[Na+].[Na+].N1C=CC=CC=1C1C=CC=CN=1>ClC(Cl)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH:29]1([N:15]2[C:11]([CH2:10][CH2:9][NH:8][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[N:12][C:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:14]2)[CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 14742,2'-BipyridineHCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 71279243HCID 71279243, compound

Product 1

HCID 86677491HCID 86677491, compoundYield 154.7%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 63651,1-DichloroethaneSolvent2×

Conditions

Temperature
85 °C

Procedure

A suspension of 5-[2-bis(tert-butoxycarbonyl)aminoethyl]-3-phenyl-[1,2,4]triazole (218 mg, 561 μmol, example 22, step 1), cyclopropylboronic acid (192.8 mg, 2.24 mmol) and sodium carbonate (119 mg, 1.12 mmol) in dichloroethane (4 mL) was evacuated and backfilled with argon. A hot suspension of copper (II) acetate (102 mg, 561 μmol) and 2,2′-bipyridine (87.6 mg, 561 μmol) in dichloroethane (1.5 mL) was added and the reaction mixture was stirred at 85° C. for 40 h. The reaction mixture was cooled to RT, filtered and washed with dichloromethane. The filtrate was extracted with water (2×20 mL), dried over MgSO4, filtered and evaporated to give 285 mg of green oil. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as colorless viscous oil (105 mg, 320 μmol, 57.0%).

Workup

  1. customwas evacuated
  2. additionwas added
  3. temperatureThe reaction mixture was cooled to RT
  4. filtrationfiltered
  5. washwashed with dichloromethane
  6. extractionThe filtrate was extracted with water (2×20 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-86f25ae935064260bed3ee9b825e0ed8
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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