1,10-Phenanthroline → HCID 25239477, compound

HRID 2170599Notes

Reaction equation

HRID 2170599 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1Br)=[O:8].C([O-])([O-])=O.[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(OCC)(=O)C>O1CCOCC1.[Cu]I>[Br:1][C:2]1[CH:17]=[C:6]([C:7]2[O:8][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=2)[CH:5]=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 1019799HCID 1019799, compound

Product 1

HCID 25239477HCID 25239477, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-N-(2-bromophenyl)nicotinamide 6 (3.44 g, 9.7 mmol), CuI (0.106 g, 0.56 mmol), Cs2CO3 (3.91 g, 12 mmol) and 1,10-phenanthroline (0.20 g, 1.12 mmol) in anhydrous 1,4-dioxane (50 ml) was heated at 100° C. overnight. After cooling to RT, the mixture was poured into ethyl acetate (200 ml), then washed with water. The aqueous phase was extracted with ethyl acetate (200 ml×2), and the organic phase was collected and dried over Na2SO4, purified by flash chromatography (silica gel, hexanes/ethyl acetate 3:1) to give a light yellow solid 7 (2.0 g, 75% yield).

Workup

  1. temperatureAfter cooling to RT
  2. washwashed with water
  3. extractionThe aqueous phase was extracted with ethyl acetate (200 ml×2)
  4. customthe organic phase was collected
  5. dry with materialdried over Na2SO4
  6. custompurified by flash chromatography (silica gel, hexanes/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-99163bf19d4a45089ba5e32400b90232
Source dataset
uspto-grants-2015_06
Patent number
US09051284B2

Reaction notes

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