2,2'-Bipyridine → HCID 57786250, 화합물

HRID 1399037노트

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HRID 1399037 반응식
[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

참가 물질

8

반응물 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

생성물 1

HCID 57786250HCID 57786250, 화합물수율 5%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
150 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e26b6984be9b48dca6b8afe07e07f234
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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