Methyl iodide → tert-Butyl 4-(6-bromo-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate

HRID 2205867노트

반응식

HRID 2205867 반응식
[H-].[Na+].[Br:3][C:4]1[N:9]=[CH:8][C:7]2[CH:10]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:17]=3)[NH:12][C:6]=2[CH:5]=1.I[CH3:26]>CN(C=O)C.O.CCOC(C)=O>[Br:3][C:4]1[N:9]=[CH:8][C:7]2[CH:10]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:17]=3)[N:12]([CH3:26])[C:6]=2[CH:5]=1

참가 물질

7

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86706280tert-Butyl 4-(6-bromo-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate

생성물 1

HCID 86706281tert-Butyl 4-(6-bromo-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate수율 78.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydride (60% in mineral oil, 7.1 mg, 0.178 mmol) was added to a solution of tert-butyl 4-(6-bromo-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate (27) (43 mg, 0.118 mmol) in DMF (515 μL) at 0° C. The reaction mixture was then stirred for 30 min at 0° C. before the addition of iodomethane (18 μL, 0.237 mmol). After stirring for 30 min, it was diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure. The crude was purified via Biotage (DCM/EtOAc 99/1 to 90/10; 12+M column) to afford the title compound as a white solid (35 mg, 78%). 1H NMR (500 MHz, CDCl3) 1.71 (s, 9H), 3.78 (s, 1H), 6.68 (d, J=0.6 Hz, 1H), 7.46 (m, 1H), 7.94 (d, J=0.6 Hz, 1H), 8.32 (d, J=0.6 Hz, 1H), 8.64 (s, 1H).

후처리

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified via Biotage (DCM/EtOAc 99/1 to 90/10; 12+M column)

출처 및 근거

ORD 기록
ord-de82d57a2f564204a6f01c931e0696eb
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371319B2

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