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

HRID 1043662ノート

反応式

HRID 1043662 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:13][C:12]3=[N:14][CH:15]=[C:16](I)[N:11]3[N:10]=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.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:13][C:12]3=[N:14][CH:15]=[C:16]([C:22]4[CH:23]=[CH:24][C:19]([OH:18])=[CH:20][CH:21]=4)[N:11]3[N:10]=2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27343604-Hydroxyphenylboronic acidHCID 67334575(4-Fluoro-phenyl)-(5-iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-amine

生成物 1

HCID 673359254-[2-(4-Fluoro-phenylamino)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-phenol収率 36%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
140 °C

実験手順

(4-Fluoro-phenyl)-(5-iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-amine (0.065 g, 0.18 mmol) was suspended in 1,4-dioxane (1 mL) at room temperature, and argon was bubbled into the mixture while tetrakis(triphenylphosphine)-palladium(0) (21 mg, 0.018 mmol), 4-hydroxyphenylboronic acid (21 mg, 0.21 mmol), cesium carbonate (118 mg, 0.36 mmol) and water (1 mL) were added. The mixture was deoxygenated for 10 minutes and heated under microwave irradiation at 140° C. for 30 minutes. On cooling, the mixture was diluted with dichloromethane (5 mL), adsorbed in silica and purified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.4:9.6 to 1:9) to give 4-[2-(4-fluoro-phenylamino)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-phenol as a beige solid (21 mg, 36% 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 (5 mL)
  5. custompurified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0.4:9.6 to 1:9)

出典と根拠

ORDレコード
ord-329077fb1ec24819bbf634ff98a09a15
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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