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

HRID 860158

反応式

HRID 860158 の反応式
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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
110 °C

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-0454f0ec6fca4761a6270e68bd5b28c6
出典データセット
uspto-grants-2006_12
特許番号
US07153874B2

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