1,2-Dichloroethane → methyl 2-bromo-7-(morpholinosulfonyl)-5H-pyrido[3,2-b]indole-4-carboxylate

HRID 2410867노트

반응식

HRID 2410867 반응식
ClCCCl.[N:5]([C:8]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[N:16][C:15]([Br:33])=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[N+]=[N-]>C(Cl)Cl.CO.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.[Rh].[Rh]>[Br:33][C:15]1[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:8]2[NH:5][C:19]3[CH:20]=[C:21]([S:24]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)(=[O:26])=[O:25])[CH:22]=[CH:23][C:18]=3[C:17]=2[N:16]=1

참가 물질

5

반응물 2

HCID 111,2-DichloroethaneHCID 86663068Methyl 3-azido-6-bromo-2-(4-(morpholinosulfonyl)phenyl)isonicotinate

생성물 1

HCID 86663069methyl 2-bromo-7-(morpholinosulfonyl)-5H-pyrido[3,2-b]indole-4-carboxylate수율 72.1%

시약·촉매·용매 2

HCID 6099591Rhodium(II) Octanoate Dimer촉매HCID 21226129Dichloromethane methanol용매

반응 조건

온도
80 °C

실험 절차

1,2-Dichloroethane (1.3 mL) was added to a mixture of methyl 3-azido-6-bromo-2-(4-(morpholinosulfonyl)phenyl)isonicotinate (918 mg, 1.90 mmol), rhodium octanoate dimer (74. mg, 0.095 mmol) and crushed 4A° molecular sieves (2.2 gm) and the reaction was heated at 80° C. overnight. It was then diluted with a mixture of DCM:MeOH (3:1) and filtered. The collected solid was washed with hot THF to extract any remaining product. The solvent was removed from the combined filtrates and the residue was suspended in MeOH. Filtration gave methyl 2-bromo-7-(morpholinosulfonyl)-5H-pyrido[3,2-b]indole-4-carboxylate (621 mg, 1.37 mmol, 72% yield) as a tan solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 12.15 (1H, s), 8.47 (1H, d, J=8.24 Hz), 8.19 (1H, s), 8.04 (1H, s), 7.65 (1H, dd, J=8.24, 1.53 Hz), 3.63-3.72 (4H, m), 2.87-3.02 (5H, m).

후처리

  1. customcrushed 4A° molecular sieves (2.2 gm)
  2. filtrationfiltered
  3. washThe collected solid was washed with hot THF
  4. extractionto extract any remaining product
  5. customThe solvent was removed from the combined filtrates
  6. filtrationFiltration

출처 및 근거

ORD 기록
ord-e1d102f3d5fc46668993cb2bca2631ad
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815840B2

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