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

HRID 2410753

反応式

HRID 2410753 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6099591Rhodium(II) Octanoate Dimer触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ae1072e84508459d90a9512f50a1bc26
出典データセット
uspto-grants-2014_08
特許番号
US08815840B2

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