1,10-Phenanthroline → HCID 15531008, compound

HRID 1883426Notes

Reaction equation

HRID 1883426 reaction equation
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].I[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36][OH:37]>[Cu]I.C1(C)C=CC=CC=1>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([O:37][CH2:36][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=2)=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 11474PiconolHCID 696764-Iodoanisole

Product 1

HCID 15531008HCID 15531008, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A test tube was charged with CuI (20 mg, 0.10 mmol, 0.10 equiv), 1,10-phenanthroline (36 mg, 0.20 mmol, 0.20 equiv), Cs2CO3 (652 mg, 2.0 mmol, 2.0 equiv), 4-iodoanisole (234 mg, 1.0 mmol, 1.0 equiv), 2-pyridylcarbinol (193 μL, 2.0 mmol, 2.0 equiv) and toluene (0.5 mL). The test tube was sealed and the reaction mixture was stirred at 110° C. for 22 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel, eluting with diethyl ether. The filtrate was concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (2×20 cm; pentane:diethyl ether 1:1) provided 120 mg (56% yield) of the title compound as a light yellow solid.

Workup

  1. customThe test tube was sealed
  2. temperatureThe resulting suspension was cooled to room temperature
  3. filtrationfiltered through a 0.5×1 cm pad of silica gel
  4. washeluting with diethyl ether
  5. concentrationThe filtrate was concentrated in vacuo
  6. customPurification of the residue by flash chromatography on silica gel (2×20 cm; pentane:diethyl ether 1:1)

Sources & evidence

ORD record
ord-6e4e3dc1e75d4c04ab2612e0e14ca452
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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