5-Bromo-N-methoxy-N-methylpyridine-3-carboxamide → (5-bromopyridin-3-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone

HRID 1753053노트

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HRID 1753053 반응식
[Si:1]([O:8][CH2:9][C:10]([N:13]1[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[C:15](I)=[CH:14]1)([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[Br:28][C:29]1[CH:30]=[N:31][CH:32]=[C:33]([CH:40]=1)[C:34](N(OC)C)=[O:35]>C1COCC1>[Br:28][C:29]1[CH:40]=[C:33]([C:34]([C:15]2[C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:21]=3[N:13]([C:10]([CH3:12])([CH3:11])[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:14]=2)=[O:35])[CH:32]=[N:31][CH:30]=1

참가 물질

5

반응물 3

HCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamideHCID 900934361-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-3-iodo-1H-pyrrolo[3,2-c]pyridineHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 90092809(5-bromopyridin-3-yl)[1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-1H-pyrrolo[3,2-c]pyridin-3-yl]methanone수율 62%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
-5 °C

실험 절차

1-(2-{[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-3-iodo-1H-pyrrolo[3,2-c]pyridine (Preparation 65, 1.81 g, 4.20 mmol) was dissolved in THF (25 mL) and the solution was degassed and cooled to −5° C. 2M iPrMgCl in THF (2.52 mL, 5.05 mmol) was added dropwise and the reaction stirred at this temperature for 45 minutes. A solution of 5-bromo-N-methoxy-N-methylnicotinamide (1.24 g, 5.05 mmol) in THF (3 mL) was added dropwise and the reaction warmed to room temperature for 4.5 hours. The reaction was partitioned between saturated aqueous ammonium chloride solution (20 mL) and EtOAc (30 mL). The organic layer was collected, dried and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 100% DCM to 50:50 DCM:EtOAc to afford the title compound as a colourless oil (1.05 g, 62%).

후처리

  1. customthe solution was degassed
  2. temperaturethe reaction warmed to room temperature for 4.5 hours
  3. customThe reaction was partitioned between saturated aqueous ammonium chloride solution (20 mL) and EtOAc (30 mL)
  4. customThe organic layer was collected
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified
  8. washeluting with 100% DCM to 50:50 DCM

출처 및 근거

ORD 기록
ord-71d1cc2d7c8448d9bcdf2ce8d3c29eb9
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09163021B2

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