2,2'-Bipyridine → HCID 57786250、化合物

HRID 1399037ノート

反応式

HRID 1399037 の反応式
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[NH:11][CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1I.N1C=CC=CC=1C1C=CC=CN=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C.[Cu]I>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:22]4[CH:21]=[CH:20][C:19]([Cl:18])=[CH:24][C:23]=4[Cl:25])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 14742,2'-BipyridineHCID 10796Cesium carbonateHCID 968642,4-Dichloro-1-iodobenzeneHCID 1363879919-Chloro-6-nitro-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole

生成物 1

HCID 57786250HCID 57786250、化合物収率 5%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

A mixture of 9-chloro-6-nitro-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole (Reference Example 108; 10.0 g, 39.6 mmol), 2,4-dichloro-1-iodobenzene (54.0 g, 197.9 mmol), copper(I) iodide (7.57 g, 39.6 mmol), 2,2′-bipyridyl (12.3 g, 79.2 mmol) and cesium carbonate (25.8 g, 79.2 mmol) in N,N-dimethylformamide (600 mL) was stirred at 150° C. for 12 hr. The mixture was diluted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 10-25% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound (750 mg, 1.88 mmol, 5%) as a light yellow amorphous.

後処理

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel eluting with a 10-25% ethyl acetate/n-hexane gradient mixture
  5. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-e26b6984be9b48dca6b8afe07e07f234
出典データセット
uspto-grants-2014_12
特許番号
US08901141B2

反応ノート

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