1,2-Dichloroethane → methyl 2-bromo-7-(4-morpholinyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylate

HRID 2410753

반응식

HRID 2410753 반응식
ClCCCl.[N:5]([C:8]1[C:9]([C:19]2[CH:20]=[N:21][C:22]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[CH:23][CH:24]=2)=[N:10][C:11]([Br:18])=[CH:12][C:13]=1[C:14]([O:16][CH3:17])=[O:15])=[N+]=[N-]>C1COCC1.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.[Rh].[Rh]>[Br:18][C:11]1[CH:12]=[C:13]([C:14]([O:16][CH3:17])=[O:15])[C:8]2[NH:5][C:20]3=[N:21][C:22]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[CH:23][CH:24]=[C:19]3[C:9]=2[N:10]=1

참가 물질

5

반응물 2

HCID 111,2-DichloroethaneHCID 86663023Methyl 3-azido-6-bromo-6'-morpholino-2,3'-bipyridine-4-carboxylate

생성물 1

HCID 86663024methyl 2-bromo-7-(4-morpholinyl)-5H-pyrido[2',3':4,5]pyrrolo[2,3-b]pyridine-4-carboxylate수율 745%

시약·촉매·용매 2

HCID 6099591Rhodium(II) Octanoate Dimer촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

1,2-Dichloroethane (0.4 mL) was added to a mixture of methyl 3-azido-6-bromo-6′-morpholino-2,3′-bipyridine-4-carboxylate (240 mg, 0.572 mmol), rhodium octanoate dimer (35.7 mg, 0.046 mmol) and crushed 4 A° molecular sieves (500 mg gm) and heated overnights at 80° C. The reaction was diluted with THF and filtered. The collected solid was washed with multiple portions of boiling THF to extract all of the product. The solvent was removed from the combined filtrates and the residue was suspended in MeOH and the product was collected by filtration. This left methyl 2-bromo-7-(4-morpholinyl)-5H-pyrido[2′,3′:4,5]pyrrolo[2,3-b]pyridine-4-carboxylate (167 mg, 0.427 mmol, 745% yield) as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 11.75 (1H, s), 8.30 (1H, d, J=8.85 Hz), 7.72 (1H, s), 6.91 (1H, d, J=8.85 Hz), 4.01 (3H, s), 3.74 (8H, dd, J=15.56, 4.88 Hz).

후처리

  1. customcrushed 4 A° molecular sieves (500 mg gm)
  2. filtrationfiltered
  3. washThe collected solid was washed with multiple portions of boiling THF
  4. extractionto extract all of the product
  5. customThe solvent was removed from the combined filtrates
  6. filtrationthe product was collected by filtration

출처 및 근거

ORD 기록
ord-ae1072e84508459d90a9512f50a1bc26
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815840B2

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