1,10-Phenanthroline → HCID 44218315, compound

HRID 1669726Notes

Reaction equation

HRID 1669726 reaction equation
I[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])=[N:7]2.[OH:22][CH2:23][CH2:24][S:25][CH3:26].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu]I.O>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[O:22][CH2:23][CH2:24][S:25][CH3:26])[N:7]=1

Participants

8

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 789252-(Methylthio)ethanolHCID 67334266HCID 67334266, compound

Product 1

HCID 44218315HCID 44218315, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

(5-Iodo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (0.3 g, 1.0 mmol) was dissolved in toluene (2 mL). After addition of 2-hydroxyethyl-methylsulfid (130 μL, 2.0 mmol), CuI (15 mg, 0.1 mmol), phenantroline (28 mg, 0.2 mmol) and caesium carbonate (0.5 g, 2.0 mmol) the reaction mixture was heated to 100° C. for 72 h. Then water was added and the mixture twice extracted with toluene. The combined organic phases were dried on sodium sulfate and evaporated. The residue was subjected to column chromatography (silica gel; heptane, ethyl acetate 10:0->3:2) to yield the title compound (75 mg, 26%) as a brown oil; MS: m/e=355.6 (M+H+).

Workup

  1. extractionthe mixture twice extracted with toluene
  2. customThe combined organic phases were dried on sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-56f85f41a05b430ebaebf91795869116
Source dataset
uspto-grants-2011_08
Patent number
US07989628B2

Reaction notes

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