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

HRID 1043662노트

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HRID 1043662 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.[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 312751,4-Dioxane용매

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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 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).

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 1:9)

출처 및 근거

ORD 기록
ord-329077fb1ec24819bbf634ff98a09a15
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563550B2

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