1,10-Phenanthroline → HCID 68435430, compound

HRID 1170140Notes

Reaction equation

HRID 1170140 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][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>C1(C)C=CC=CC=1.[Cu]I>[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][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:7]=1

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 696852-(Phenylthio)ethanolHCID 67334266HCID 67334266, compound

Product 1

HCID 68435430HCID 68435430, compoundYield 96%

Reagents, catalysts & solvents 2

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

Procedure

(5-Iodo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (0.4 g, 1 mMol) and 2-hydroxyethyl-phenylsulfide (0.32 g, 2 mMol) were heated in toluene together with CuI (10 Mol-%), phenantroline (20 Mol-%) and CsCO3 (0.67 g, 2 mMol) to 100° C. for 24 h. After cooling to ambient temperature the reaction mixture was extracted twice with toluene, the combined organic phases were extracted with water and subsequently dried with sodium sulfate. After evaporation the residue was subjected to column chromatography (silica gel, heptane/ethyl acetate 100:0->60:40 gradient) to yield (2-methoxy-benzyl)-[5-(2-phenylsulfanyl-ethoxy)-quinolin-2-yl]-amine (0.4 g, 93%) as a yellow oil,

Workup

  1. extractionwas extracted twice with toluene
  2. extractionthe combined organic phases were extracted with water
  3. dry with materialsubsequently dried with sodium sulfate
  4. customAfter evaporation the residue

Sources & evidence

ORD record
ord-e14d083bad1e4e5c894c75f8d60ecb55
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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