1,10-Phenanthroline → HCID 21940731, compound

HRID 1883341Notes

Reaction equation

HRID 1883341 reaction equation
[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2N=CC=C3)C=C[CH:2]=1.CC(C)([O-])C.[Na+].CCCCCCCCCCCC.I[C:34]1[CH:35]=[C:36]([CH3:41])[CH:37]=[C:38]([CH3:40])[CH:39]=1.CNC1C=CC=CC=1>[Cu]I.O1CCOCC1>[CH3:40][C:38]1[CH:39]=[C:34]([N:1]([CH3:2])[C:14]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:13]=2)[CH:35]=[C:36]([CH3:41])[CH:37]=1

Participants

8

Reactant 5

HCID 13181,10-PhenanthrolineHCID 7515N-MethylanilineHCID 8182DodecaneHCID 1409241-Iodo-3,5-dimethylbenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 21940731HCID 21940731, compoundYield 469%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

An oven-dried resealable Schlenk tube was charged with CuI (10 mg, 0.0525 mmol, 5.0 mol %), 1,10-phenanthroline (20 mg, 0.111 mmol), sodium tert-butoxide (145 mg, 1.51 mmol), evacuated and backfilled with argon. Dodecane (235 μL), 5-iodo-m-xylene (150 μL, 1.04 mmol), N-methylaniline (135 μL, 1.25 mmol) and dioxane (1.0 mL) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting brown suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×15 cm; hexane-ether 50:1; 10 mL fractions). Fractions 7-11 provided 110 mg (50% yield) of the product as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.33−7.27 (m, 2H), 7.05−6.94 (m, 3H), 6.72 (s, 2H), 6.68 (s, 1H), 3.33 (s, 3H), 2.31 (s, 6H).

Workup

  1. customevacuated
  2. customThe Schlenk tube was sealed
  3. temperatureThe resulting brown suspension was cooled to room temperature
  4. filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by flash chromatography on silica gel (2×15 cm; hexane-ether 50:1; 10 mL fractions)

Sources & evidence

ORD record
ord-f58639608d73412cbbc908834b22609f
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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