1,10-Phenanthroline → HCID 44219391, compound

HRID 1671561Notes

Reaction equation

HRID 1671561 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3I)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH:22][CH2:23][CH2:24][S:25][CH3:26].C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>C1(C)C=CC=CC=1.[Cu](I)I>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[O:22][CH2:23][CH2:24][S:25][CH3:26])[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 789252-(Methylthio)ethanolHCID 67095932HCID 67095932, compound

Product 1

HCID 44219391HCID 44219391, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

(R)-Indan-1-yl-(5-iodo-quinolin-2-yl)-amine (250 mg, 0.6 mmol) were dissolved in toluene (2 mL). 2-Hydroxyethyl-methylsulfide (0.17 □L, 1.8 mmol), copper iodide (12 mg), cesium carbonate (420 mg, 1.2 mmol) and phenantroline (23 mg) were added. The reaction mixture was stirred for 48 h at 110° C. The reaction mixture was extracted with water (2×10 mL). The organic phase was 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 as brown oil (80 mg, 35%); MS: m/e=351.6 (M+H+).

Workup

  1. extractionThe reaction mixture was extracted with water (2×10 mL)
  2. customThe organic phase was dried on sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-712a510ca68b47cbb883d545c5db65a4
Source dataset
uspto-grants-2011_08
Patent number
US07994324B2

Reaction notes

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