Nitrogen → 3-(4-chloropyrimidin-2-yl)-5-(2,6-difluorophenyl)-1-tosyl-1H-indole

HRID 1529304노트

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HRID 1529304 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([S:18]([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH:13]=[C:12]2I.[Cl:29][C:30]1[CH:35]=[CH:34][N:33]=[C:32]([Sn](CCCC)(CCCC)CCCC)[N:31]=1.N#N>CN(C=O)C.[Cu]I.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>[Cl:29][C:30]1[CH:35]=[CH:34][N:33]=[C:32]([C:12]2[C:11]3[C:15](=[CH:16][CH:17]=[C:9]([C:3]4[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=4[F:8])[CH:10]=3)[N:14]([S:18]([C:21]3[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:13]=2)[N:31]=1

참가 물질

7

반응물 3

HCID 947NitrogenHCID 149763044-Chloro-2-(tributylstannyl)pyrimidineHCID 679602665-(2,6-difluorophenyl)-3-iodo-1-tosyl-1H-indole

생성물 1

HCID 867097683-(4-chloropyrimidin-2-yl)-5-(2,6-difluorophenyl)-1-tosyl-1H-indole수율 26%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a solution of 5-(2,6-difluorophenyl)-3-iodo-1-tosyl-1H-indole (2.0 g, 3.92 mmol) and 4-chloro-2-tributylstannanyl-pyrimidine (2.38 g, 5.98 mmol) in DMF (60 mL) was bubbled N2 for 15 min and added CuI (0.898 g, 4.71 mmol) and Pd(PPh3)4 (0.226 g, 0.196 mmol). The reaction mixture was heated at 80° C. for 1 h and cooled to RT. The reaction mixture was quenched with water and precipitate was formed. The resulting precipitate was collected by filtration, washed with water, and dried to yield crude product. Purification by silica gel column chromatography, eluting with 10% EtOAc in hexanes obtained the title compound (0.50 g, 26%). MS (ESI, pos. ion) m/z: 496.0 (M+1).

후처리

  1. temperaturecooled to RT
  2. customThe reaction mixture was quenched with water
  3. customprecipitate was formed
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried
  7. customto yield crude product
  8. customPurification by silica gel column chromatography
  9. washeluting with 10% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-35084e243d854caa8a72d4544b797032
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090593B2

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