Water → Methyl 3-(5-((5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)-4-fluorobenzoate

HRID 1645279

반응식

HRID 1645279 반응식
Br[C:2]1[O:6][C:5]([CH:7]=[C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=3)[NH:10][C:9]2=[O:18])=[CH:4][CH:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][C:21]=1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+].O>O1CCOCC1.O.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[Cl:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:18])[C:8]2=[CH:7][C:5]1[O:6][C:2]([C:21]2[CH:22]=[C:23]([CH:24]=[CH:25][C:20]=2[F:19])[C:26]([O:28][CH3:29])=[O:27])=[CH:3][CH:4]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 230053662-Fluoro-5-(methoxycarbonyl)benzeneboronic acidHCID 667728293-((5-Bromofuran-2-yl)methylene)-5-chloroindolin-2-one

생성물 1

HCID 66772226Methyl 3-(5-((5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)-4-fluorobenzoate

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
110 °C

실험 절차

To 3-((5-bromofuran-2-yl)methylene)-5-chloroindolin-2-one (150 mg, 0.466 mmol) in dioxane/water (2850/150 μL) was added 2-fluoro-5-(methoxycarbonyl)phenylboronic acid (111 mg, 0.559 mmol) and Cs2CO3 (456 mg, 1.398 mmol). The mixture was degassed with nitrogen for 5 minutes, then PdCl2 dppf (17 mg, 0.023 mmol) was added. The mixture was heated in microwave for 40 minutes at 110° C. Water was added and the solid formed was isolated by filtration to yield methyl 3-(5-((5-chloro-2-oxoindolin-3-ylidene)methyl)furan-2-yl)-4-fluorobenzoate. LCMS (M+1=398).

후처리

  1. customThe mixture was degassed with nitrogen for 5 minutes
  2. customthe solid formed
  3. customwas isolated by filtration

출처 및 근거

ORD 기록
ord-082e5aabf5664a4ea69bcaaea55ec8d4
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124649B2

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