1,10-Phenanthroline → HCID 86711726, compound

HRID 516491Notes

Reaction equation

HRID 516491 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2Br)=[O:19])[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>[Cu]I.O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:18]2[O:19][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]=2)[CH:5]=[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:17]=1

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 86711725HCID 86711725, compound

Product 1

HCID 86711726HCID 86711726, compoundYield 88.5%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
120 °C

Procedure

A mixture of Compound 10 (20.3 g, 36.7 mmol), CuI (0.700 g, 3.67 mmol), Cs2CO3 (23.9 g, 73.5 mmol), 1,10-phenanthroline (1.32 g, 7.35 mmol) and 1,4-dioxane (300 mL) was degassed with Ar and then maintained at about 120° C. overnight. Upon confirming consumption of the starting material by TLC (SiO2, 4:1 hexanes-ethyl acetate), the reaction was cooled to RT and diluted with EtOAc (ca. 300 mL) and H2O (ca. 400 mL). The resulting suspension was then filtered and the filtrant washed copiously with H2O and CH3OH to provide Compound 11 (12.7 g, 88%) as an off-white solid: confirmed by LCMS (APCI): calculated for C20H11BrN2O2 (M+): 391; Found: 391.

Workup

  1. customwas degassed with Ar
  2. customconsumption of the starting material by TLC (SiO2, 4:1 hexanes-ethyl acetate)
  3. temperaturethe reaction was cooled to RT
  4. additiondiluted with EtOAc (ca. 300 mL) and H2O (ca. 400 mL)
  5. filtrationThe resulting suspension was then filtered
  6. washthe filtrant washed copiously with H2O and CH3OH

Sources & evidence

ORD record
ord-c29ee17113c94577904b1e7ea0d0af32
Source dataset
uspto-grants-2015_08
Patent number
US09112159B2

Reaction notes

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