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

HRID 79614

反応式

HRID 79614 の反応式
[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

参加物

8

反応物 5

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 602052765-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine

生成物 1

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

試薬・触媒・溶媒 2

HCID 3939Lithium Hydroxide溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5061f5e55d624c41b472ecbf109cce71
出典データセット
uspto-grants-2014_09
特許番号
US08841304B2

関連ノート

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