Water → N-{4-[2-(4-fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-phenyl}-acetamide

HRID 1043659ノート

反応式

HRID 1043659 の反応式
[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[S:11][C:10]3=[N:12][CH:13]=[C:14](I)[N:9]3[N:8]=2)=[CH:4][CH:3]=1.[C:18]([NH:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)(=[O:20])[CH3:19].C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C>[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[S:11][C:10]3=[N:12][CH:13]=[C:14]([C:25]4[CH:26]=[CH:27][C:22]([NH:21][C:18](=[O:20])[CH3:19])=[CH:23][CH:24]=4)[N:9]3[N:8]=2)=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27346574-Acetamidophenylboronic acidHCID 673357762-(4-Fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole

生成物 1

HCID 67335431N-{4-[2-(4-fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-phenyl}-acetamide収率 43%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 3283Diethyl Ether溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
140 °C

実験手順

2-(4-Fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole (0.15 g, 0.42 mmol) was suspended in 1,4-dioxane (1.5 mL) at room temperature and argon was bubbled into the mixture while dichlorobis(triphenylphosphine)palladium(II) (29 mg, 0.042 mmol), 4-acetamidophenylboronic acid (85 mg, 0.48 mmol), cesium carbonate (271 mg, 0.83 mmol) and water (1.5 mL) were added. The mixture was deoxygenated for 10 minutes and heated under microwave irradiation at 140° C. for 20 minutes. On cooling, the resulting suspension was diluted with dichloromethane (7 mL), adsorbed in silica and purified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.2:9.8 to 2:8). The residue obtained was treated with diethylether (7 mL) and filtered to give 66 mg of N-{4-[2-(4-fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-phenyl}-acetamide as a white solid (43%).

後処理

  1. additionwere added
  2. customThe mixture was deoxygenated for 10 minutes
  3. temperatureOn cooling
  4. additionthe resulting suspension was diluted with dichloromethane (7 mL)
  5. custompurified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.2:9.8 to 2:8)
  6. customThe residue obtained
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-f7536b47433241f3b5a7a25400d8c874
出典データセット
uspto-grants-2013_10
特許番号
US08563550B2

反応ノート

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