Water → 3-Phenyl-7-(4-pyridyl)imidazo[1,2-a]pyridine

HRID 1245483노트

반응식

HRID 1245483 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.Br[CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:16]=O.C([O-])(O)=O.[Na+].O>O1CCOCC1>[C:18]1([C:15]2[N:3]3[CH:4]=[CH:5][C:6]([C:8]4[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=4)=[CH:7][C:2]3=[N:1][CH:16]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 108889012-Bromo-2-phenylacetaldehydeHCID 21912841[4,4'-Bipyridin]-2-amine

생성물 1

HCID 219128683-Phenyl-7-(4-pyridyl)imidazo[1,2-a]pyridine

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To the solution of 2-amino-4,4′-bipyridine (0.482 g, 2.815 mmol, 1 equiv) in dioxane (14 mL) was added bromophenylacetaldehyde (0.897 g, 4.50 mmol, 1.6 equiv) and NaHCO3 (0.473 g, 5.63 mmol, 2 equiv). The suspension was stirred at rt for 30 min and then heated to 80° C. for 6 h. The reaction mixture was poured into water and extracted with EtOAc. The combined organic layer was dried, concentrated and purified by flash column chromatography (5% MeOH in CH2Cl2 ) to give 3-phenyl-7-(4-pyridyl)imidazo[1,2-a]pyridine as a solid. 1H NMR (CDCl3) δ 8.72 (d, 2H, J=6.1), 8.45 (d, 1H, J=7.3), 8.00 (s, 1H), 7.80 (s, 1H), 7.61–7.55 (m, 6H), 7.48–7.44 (m, 1H), 7.14 (d, 1H, J=7.3); LRMS m/z (M+H) Calcd: 272.3, found: 272.2.

후처리

  1. temperatureheated to 80° C. for 6 h
  2. extractionextracted with EtOAc
  3. customThe combined organic layer was dried
  4. concentrationconcentrated
  5. custompurified by flash column chromatography (5% MeOH in CH2Cl2 )

출처 및 근거

ORD 기록
ord-aaf422dbf9014809ae35675a6384a86c
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07125888B2

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