1,10-Phenanthroline → 2-Methoxy-4-[2-methyl-4-(2-methyl-pyridin-4-ylethynyl)-imidazol-1-yl]-pyridine

HRID 860158

Reaction equation

HRID 860158 reaction equation
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:39][C:40]1[CH:45]=[C:44]([C:46]#[C:47][C:48]2[N:49]=[C:50]([CH3:53])[NH:51][CH:52]=2)[CH:43]=[CH:42][N:41]=1.I[C:55]1[CH:60]=[CH:59][N:58]=[C:57]([O:61][CH3:62])[CH:56]=1>CC1C=CC=CC=1C>[CH3:62][O:61][C:57]1[CH:56]=[C:55]([N:51]2[CH:52]=[C:48]([C:47]#[C:46][C:44]3[CH:43]=[CH:42][N:41]=[C:40]([CH3:39])[CH:45]=3)[N:49]=[C:50]2[CH3:53])[CH:60]=[CH:59][N:58]=1

Participants

7

Reactant 5

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 95417Dibenzylidene acetoneHCID 150197954-Iodo-2-methoxypyridineHCID 178418884HCID 178418884, compound

Product 1

HCID 100863752-Methoxy-4-[2-methyl-4-(2-methyl-pyridin-4-ylethynyl)-imidazol-1-yl]-pyridine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
110 °C

Procedure

Following the Buchwald-protocol [Buchwald et al., Tetrahedron Lett. 40:2657 (1999)], a rigorously dried Schlenk tube was filled with argon and charged with copper(I) trifluoromethanesulfonate benzene complex (101 mg, 0.2 mmol), phenanthroline (720 mg, 4.0 mmol), dibenzylideneacetone (47 mg, 0.2 mmol) and cesium carbonate (2.86 g, 8.8 mmol). 2-Methyl-4-(2-methyl-1H-imidazol-4-ylethynyl)-pyridine (II-1) (1.18 g, 6.0 mmol), o-xylene (1.6 ml) and 4-iodo-2-methoxypyridine x HCl (1.1 g, 4.0 mmol) [Talik and Plazek, Rocz. Chem. 33:1343 (1959)] was added. The mixture was stirred at 110° C. for 24 hr, cooled to RT and partitioned between CH2Cl2 and saturated aqueous NH4Cl solution. The organic phase was concentrated and purified by chromatography on silica gel (dichloromethane/methanol 100:0→97:3 gradient). The title compound was obtained as a tan semisolid material (44 mg, 4%). The free base was converted to the HCL salt. mp=145–147° C. (MeOH/Et2O), MS: m/e=305.0 (M+H+).

Workup

  1. additiona rigorously dried Schlenk tube was filled with argon
  2. temperaturecooled to RT
  3. custompartitioned between CH2Cl2 and saturated aqueous NH4Cl solution
  4. concentrationThe organic phase was concentrated
  5. custompurified by chromatography on silica gel (dichloromethane/methanol 100:0→97:3 gradient)

Sources & evidence

ORD record
ord-0454f0ec6fca4761a6270e68bd5b28c6
Source dataset
uspto-grants-2006_12
Patent number
US07153874B2

Linked notes

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