2,2'-Bipyridine → HCID 102065214, compound

HRID 1050646Notes

Reaction equation

HRID 1050646 reaction equation
[CH:1]1[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3][CH:2]=1.N1C=CC=[CH:11][C:10]=1[C:15]1C=CC=CN=1.BrC1C=C2C(C)(C)C3C=CC=[C:39]4[C:40](C)(C)[C:30]5[C:31]6N(C=34)C2=[C:24]([C:25](C)(C)[C:26]=6[CH:27]=[CH:28][CH:29]=5)[CH:23]=1>CN(C)C=O.C1(C)C=CC=CC=1>[CH2:15]1[C:6]2=[CH:7][CH:8]=[CH:1][C:4]3=[CH:3][C:2]4=[C:27]5[C:28](=[C:5]23)[C:29]2[C:30]([CH2:31][C:26]5=[CH:25][CH:24]=[CH:23]4)=[CH:40][CH:39]=[CH:11][C:10]1=2

Participants

6

Reactant 3

HCID 14742,2'-BipyridineHCID 8135cis,cis-1,5-CyclooctadieneHCID 70885920HCID 70885920, compound

Product 1

HCID 102065214HCID 102065214, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Bis(1,5-cycloocatadiene)nickel(0) (0.193 g, 0.70 mmol), 1,5-cyclooctadiene (0.08 g, 0.09 mL, 0.70 mmol) and 2,2′-bipyridine (0.109 g, 0.70 mmol) were added to a flame-dried 100 mL Schlenk flask, dissolved in 9.4 mL of anhydrous N,N-dimethylformamide and stirred for 30 min at 65° C. in the absence of light. A solution of 2-bromo-4,4,8,8,12,12-hexamethyl-8,12-dihydro-4H-benzo[1,9]quinolizino[3,4,5,6,7-defg]acridine (0.25 g, 0.56 mmol) in 18.8 mL of anhydrous toluene at 65° C. was added slowly via a double-tipped needle and the resulting mixture was stirred for two days at 85° C. The reaction was quenched by adding 10% aqueous hydrochloric acid, extracted three times with CH2Cl2 and the organic phase was dried with MgSO4. After having removed the solvents in vacuo, the residue was subjected to column chromatography (silice, n-hexane/CH2Cl2 3:1) leading to triangulene dimer as a white crystalline solid (0.165 g, 80%).

Workup

  1. stirringthe resulting mixture was stirred for two days at 85° C
  2. customThe reaction was quenched
  3. additionby adding 10% aqueous hydrochloric acid
  4. extractionextracted three times with CH2Cl2
  5. dry with materialthe organic phase was dried with MgSO4
  6. customAfter having removed the solvents in vacuo

Sources & evidence

ORD record
ord-0db83757ab3d4a48ae84d6a7f6e20685
Source dataset
uspto-grants-2016_07
Patent number
US09385326B2

Reaction notes

Loading…