1,10-Phenanthroline → HCID 44477077, compound

HRID 2361655Notes

Reaction equation

HRID 2361655 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([CH:6]=[O:7])[CH2:3]1.I[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.C([O-])([O-])=O.[Cs+].[Cs+].[N:23]1[C:36]2C(=CC=[C:30]3[C:35]=2[N:34]=[CH:33][CH:32]=[CH:31]3)[CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1.[Cu]I>[CH:33]1([N:34]2[CH2:26][CH2:25][CH2:24][N:23]([C:6]([N:4]3[CH2:5][CH:2]([O:1][C:9]4[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=4)[CH2:3]3)=[O:7])[CH2:36][CH2:35]2)[CH2:32][CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 696764-IodoanisoleHCID 53677339HCID 53677339, compound

Product 1

HCID 44477077HCID 44477077, compoundYield 187.8%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

To a stirred suspension of 4-cyclobutyl-[1,4]diazepan-1-yl)-(3-hydroxy-azetidin-1-yl)-methanone (50 mg, 0.197 mmol) in toluene (2 ml) was added 4-iodoanisole (69 mg, 0.296 mmol), Cs2CO3 (128 mg, 0.394 mmol), CuI (3.7 mg, 0.0197 mmol) and 1,10-phenanthroline (7.1 mg, 0.04 mmol). The resulting mixture was heated at 100° C. overnight, then cooled to RT and filtered through a plug of silica gel, eluting with EtOAc. The filtrate was concentrated in vacuo and the residue purified by FCC [silica, eluting with DCM/MeOH/NH3; 90:10:1] to provide the title compound as colourless oil (27 mg, 39%).

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered through a plug of silica gel
  3. washeluting with EtOAc
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue purified by FCC [silica, eluting with DCM/MeOH/NH3; 90:10:1]

Sources & evidence

ORD record
ord-e71ac98779fd4e9dab0f8abd91ecea1d
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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