烟酸 → N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide

HRID 79614

反应方程式

HRID 79614 反应方程式
[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH2:11])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[C:13](O)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C(N(CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.[Li+].[OH-]>[Br:1][C:2]1[C:3]([F:12])=[C:4]2[C:10]([NH:11][C:13](=[O:20])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

参与物

8

反应物 5

HCID 938烟酸HCID 8471三乙胺HCID 10340Carbonic acid sodium salt (1:2)HCID 152842双(2-氧代-3-恶唑烷基)次磷酰氯HCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

产物 1

HCID 60205277N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide收率 55%

试剂、催化剂与溶剂 2

HCID 3939氢氧化锂溶剂HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

5-Bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (0.044 g, 0.19 mmol), nicotinic acid (0.0283 g, 0.230 mmol), and BOP-Cl (0.0584 g, 0.230 mmol) were placed in DMF (3 mL) at room temperature. Triethylamine (0.133 mL, 0.956 mmol) was then added, and the reaction was stirred for 1 hour at room temperature. The reaction was then diluted with 3M LiOH (aq., 0.5 mL) and stirred for 10 minutes. The reaction was then poured into saturated Na2CO3, extracted into DCM, and the organic fractions were combined, dried, filtered and concentrated to give a crude residue. The crude residue was triturated with 1:2 MeOH/DCM to give N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.035 g, 54.6% yield) as a solid.

后处理

  1. stirringstirred for 10 minutes
  2. extractionextracted into DCM
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude residue
  7. customThe crude residue was triturated with 1:2 MeOH/DCM

来源与证据

ORD记录
ord-5061f5e55d624c41b472ecbf109cce71
来源数据集
uspto-grants-2014_09
专利号
US08841304B2

关联笔记

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