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

HRID 2410867ノート

反応式

HRID 2410867 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6099591Rhodium(II) Octanoate Dimer触媒HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e1d102f3d5fc46668993cb2bca2631ad
出典データセット
uspto-grants-2014_08
特許番号
US08815840B2

反応ノート

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