Cesium carbonate → 2-Chloro-4-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-pyridine

HRID 2194384노트

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HRID 2194384 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:15])[NH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:16][C:17]1[CH:22]=[C:21](F)[CH:20]=[CH:19][N:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:16][C:17]1[CH:22]=[C:21]([N:13]2[CH:14]=[C:10]([C:9]#[C:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[N:11]=[C:12]2[CH3:15])[CH:20]=[CH:19][N:18]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 27827922-Chloro-4-fluoropyridineHCID 178432693HCID 178432693, 화합물

생성물 1

HCID 866498792-Chloro-4-[4-(3-chloro-phenylethynyl)-2-methyl-imidazol-1-yl]-pyridine수율 88%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a solution of 400 mg (1.85 mmol) of 4-(3-chloro-phenylethynyl)-2-methyl-1H-imidazole and 1.12 ml (1.46 g, 11.1 mmol) of 2-chloro-4-fluoropyridine in 5 ml of DMF were added 1.2 g (3.69 mmol) of cesium carbonate. The mixture was heated to 100° C. for 4 h, allowed to cool and concentrated in vaccuo. The residue was taken up in 20 ml ethyl acetate and the organic phase was washed twice with 20 ml of water and dried over magnesium sulfate. After treatment with charcoal, the solution was filtered and concentrated to yield 531 mg (1.62 mmol, 88%) of the title compound as an off-white crystalline solid, MS: m/e=328.1, 330.1 (M+H+).

후처리

  1. temperatureto cool
  2. concentrationconcentrated in vaccuo
  3. washthe organic phase was washed twice with 20 ml of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter treatment with charcoal, the solution was filtered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e845b2b862474653b7eb8a40a0d92c37
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334287B2

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