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

HRID 1043663노트

반응식

HRID 1043663 반응식
[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.[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:7]=[CH:6][C:5]([NH:8][C:9]2[S:13][C:12]3=[N:14][CH:15]=[C:16]([C:25]4[CH:26]=[CH:27][C:22]([NH:21][C:18](=[O:20])[CH3:19])=[CH:23][CH:24]=4)[N:11]3[N:10]=2)=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27346574-Acetamidophenylboronic acidHCID 67334575(4-Fluoro-phenyl)-(5-iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-amine

생성물 1

HCID 67336560N-{4-[2-(4-fluoro-phenylamino)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-phenyl}-acetamide수율 15.1%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 3283Diethyl Ether용매HCID 312751,4-Dioxane용매

반응 조건

온도
140 °C

실험 절차

(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 dichlorobis(triphenylphosphine)-palladium(II) (13 mg, 0.018 mmol), 4-acetamidophenylboronic acid (37 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 1.5:8.5). The product obtained was treated with diethylether (7 mL) and filtered to give N-{4-[2-(4-fluoro-phenylamino)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-phenyl}-acetamide as an off-white solid (10 mg, 15% yield).

후처리

  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 1.5:8.5)
  6. customThe product obtained
  7. filtrationfiltered

출처 및 근거

ORD 기록
ord-1b326fabc8884ec9a8edae587076695b
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563550B2

반응 노트

불러오는 중…