1,10-Phenanthroline → HCID 67436320, compound

HRID 1663588Notes

Reaction equation

HRID 1663588 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[N:9]2[CH2:13][CH2:12][C@@H:11]([NH:14][C:15](=[O:23])[C:16]3[CH:21]=[C:20](Br)[CH:19]=[N:18][CH:17]=3)[CH2:10]2)=[CH:4][CH:3]=1.[C:31](=[O:34])([O-])[O-].[Cs+].[Cs+].[I-].[Na+].N1C2C(=CC=C3C=2N=CC=C3)C=C[CH:40]=1>C1(C)C=CC=CC=1.[Cu](I)I.C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[N:9]2[CH2:13][CH2:12][C@@H:11]([NH:14][C:15](=[O:23])[C:16]3[CH:21]=[C:20]([O:34][CH2:31][CH3:40])[CH:19]=[N:18][CH:17]=3)[CH2:10]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 13181,10-PhenanthrolineHCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 67436462HCID 67436462, compound

Product 1

HCID 67436320HCID 67436320, compoundYield 55.4%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (3R)-1-[bis-(4-chlorophenyl)methyl]-3-[(5-bromonicotinoyl)-amino]pyrrolidine (50 mg) in toluene was added copper iodide (7 mg), cesium carbonate (15 mg), sodium iodide (15 mg), phenanthroline (14 mg) and ethanol (0.1 mL) and the mixture was stirred at 100° C. for 15 hours. The reaction mixture was evaporated in vacuo and to the residue was added an aqueous saturated sodium hydrogencarbonate solution was added. The mixture was extracted with ethyl acetate and the organic layer was evaporated in vacuo. The residue was purified by a column chromatography on silica gel (solvent; ethyl acetate/hexane=1:1) to give (3R)-1-[bis-(4-chlorophenyl)methyl]-3-[(5-ethoxynicotinoyl)amino]pyrrolidine (12 mg, yield: 26%) as a powder.

Workup

  1. customThe reaction mixture was evaporated in vacuo and to the residue
  2. additionwas added an aqueous saturated sodium hydrogencarbonate solution
  3. additionwas added
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe organic layer was evaporated in vacuo
  6. customThe residue was purified by a column chromatography on silica gel (solvent; ethyl acetate/hexane=1:1)

Sources & evidence

ORD record
ord-dead181a2fc6419b8f1fe76d6483084b
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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