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Dimethylformamide → 4-(4-((3-chloroimidazo[1,2-a]pyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one

HRID 1842421
ノート
印刷プレビュー

反応式

HRID 1842421 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:23])[C:10]([CH3:22])([CH3:21])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.[Cl:35][C:36]1[N:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]2=[N:38][C:37]=1[CH2:45]Cl>O>[Cl:35][C:36]1[N:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]2=[N:38][C:37]=1[CH2:45][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:23])[C:10]([CH3:21])([CH3:22])[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 595801634-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-oneHCID 595801663-Chloro-2-(chloromethyl)imidazo[1,2-a]pyridine

生成物 1

HCID 497791154-(4-((3-chloroimidazo[1,2-a]pyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one収率 82.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

4-(4-Hydroxyphenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (200 mg, 0.64 mmol) was added to a mixture of cesium carbonate (843 mg, 2.5 mmol) and DMF (20 mL) at RT under an atmosphere of nitrogen. The reaction mixture was stirred at RT for 30 min, upon which 3-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine (183 mg, 0.77 mmol) was added. The mixture was heated at 80° C. for 4 h (the reaction was monitored by TLC) upon which, the mixture was diluted with water and extracted with EtOAc. The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography using 18% ethyl acetate in n-hexane and silica gel (230-400 mesh) to afford 4-(4-((3-chloroimidazo[1,2-a]pyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (250 mg, 81%,) as an off-white solid. 1H NMR: 500 MHz, DMSO-d6: δ 8.4 (d, 1H), 7.7 (d, 1H), 7.55 (Ar, 3H), 7.7-6.9 (Ar, 10H), 5.2 (s, 2H) 3.8 (s, 3H), 1.4 (s, 6H). MS: [M+H]+: m/z=470.7. HPLC: (97.2%, Condition-A).

後処理

  1. additionwas added
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-08295ac4064e462f90378020feef100c
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08946222B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート