Water → 4-[2-(4-Fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-phenol

HRID 1043658ノート

反応式

HRID 1043658 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.[OH:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClCCl>[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:22]4[CH:23]=[CH:24][C:19]([OH:18])=[CH:20][CH:21]=4)[N:9]3[N:8]=2)=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27343604-Hydroxyphenylboronic acidHCID 673357762-(4-Fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole

生成物 1

HCID 673343104-[2-(4-Fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-phenol収率 27%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane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 tetrakis(triphenylphosphine)palladium(0) (48 mg, 0.042 mmol), 4-hydroxyphenylboronic acid (66 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 mixture was diluted with dichloromethane (7 mL), adsorbed in silica and purified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.2:9.8 to 1.5:7.5). The product obtained was treated with dichloromethane (5 mL) and filtered to give 4-[2-(4-fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-phenol as a white solid (37 mg, 27% yield).

後処理

  1. additionwere added
  2. customThe mixture was deoxygenated for 10 minutes
  3. temperatureOn cooling
  4. additionthe mixture was diluted with dichloromethane (7 mL)
  5. custompurified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.2:9.8 to 1.5:7.5)
  6. customThe product obtained
  7. filtrationfiltered

出典と根拠

ORDレコード
ord-b6f5612227384747a28c3e8261a7c500
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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