1,2-Diaminocyclohexane, trans- → methyl 1-(3-(dimethylamino)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

HRID 1766164노트

반응식

HRID 1766164 반응식
P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[N:13]([CH3:15])[CH3:14].[C@@H]1(N)CCCC[C@H]1N.[NH:27]1[C:31]2=[N:32][CH:33]=[CH:34][CH:35]=[C:30]2[C:29]([C:36]([O:38][CH3:39])=[O:37])=[CH:28]1>CCCCCCCCCCCC.O1CCOCC1.ClCCl>[CH3:14][N:13]([CH3:15])[C:12]1[CH:11]=[C:10]([N:27]2[C:31]3=[N:32][CH:33]=[CH:34][CH:35]=[C:30]3[C:29]([C:36]([O:38][CH3:39])=[O:37])=[CH:28]2)[CH:18]=[CH:17][CH:16]=1

참가 물질

8

반응물 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 1401023-Bromo-N,N-dimethylanilineHCID 21110084methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate

생성물 1

HCID 21110081methyl 1-(3-(dimethylamino)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8182Dodecane용매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

0.038 g (0.2 mmol) of cuprous iodide, 0.891 g (4.2 mmol) of potassium phosphate, 0.40 g (2 mmol) of 3-bromo-N,N-dimethylaniline and 0.24 cm3 (2 mmol) of trans-1,2-cyclohexanediamine were added, under an argon atmosphere, to 0.405 g (2.3 mmol) of methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate in solution in 0.3 cm3 of dodecane and 6 cm3 of dioxane. After stirring at a temperature in the region of 110° C. for 48 h, the reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which was taken up in 20 cm3 of dichloromethane. The resulting organic solution was washed with 20 cm3 of 0.1N hydrochloric acid and filtered, then dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). Methyl 1-(3-(dimethylamino)phenyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate, characterized by LC/MS (m/z 296 [MH]+), was thus obtained, which was used directly in the following stage.

후처리

  1. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa)
  2. customto give a residue which
  3. washThe resulting organic solution was washed with 20 cm3 of 0.1N hydrochloric acid
  4. filtrationfiltered
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customwas thus obtained

출처 및 근거

ORD 기록
ord-7210c726eaa1435bb6e0a3a64f3699f1
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230007B2

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