Sodium Carbonate → 3-(2,6-dichloropyridin-4-yl)-5-methoxy-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2089017

반응식

HRID 2089017 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:11](B3OC(C)(C)C(C)(C)O3)=[CH:10][N:9]([S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:6]2=[N:7][CH:8]=1.[Cl:30][C:31]1[CH:36]=[C:35](I)[CH:34]=[C:33]([Cl:38])[N:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.CCO.O.O.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>[Cl:30][C:31]1[CH:36]=[C:35]([C:11]2[C:5]3[C:6](=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]([S:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)(=[O:23])=[O:22])[CH:10]=2)[CH:34]=[C:33]([Cl:38])[N:32]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 117373932,6-Dichloro-4-iodopyridineHCID 668892775-Methoxy-1-(phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 871925543-(2,6-dichloropyridin-4-yl)-5-methoxy-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine수율 56%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 86587095Dimethoxyethane ethanol water용매

반응 조건

온도
80 °C

실험 절차

A suspension of Example 149c (0.150 g, 0.362 mmol), 2,6-dichloro-4-iodopyridine (0.099 g, 0.362 mmol), dichlorobis(triphenylphosphine)palladium(II) (10.17 mg, 0.014 mmol) and 1M sodium carbonate (0.290 mL, 0.290 mmol) in dimethoxyethane/EtOH/water (7:2:3, 2.5 mL) was degassed and heated at 80° C. overnight. After cooling, the suspension was diluted with water and extracted with EtOAc (2×). The suspension in the aq. layer was filtered, washed with water, and dried to give 88.0 mg of the title compound

후처리

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc (2×)
  3. filtrationThe suspension in the aq. layer was filtered
  4. washwashed with water
  5. customdried

출처 및 근거

ORD 기록
ord-18cb2881cc434b15bb93ad7040602c4b
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08435980B2

연결된 노트

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