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

HRID 860158

반응식

HRID 860158 반응식
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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 7237O-Xylene용매

반응 조건

온도
110 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-0454f0ec6fca4761a6270e68bd5b28c6
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153874B2

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