Water → 5-(4-Pyridinyl)-1H-pyrrolo(2,3-b)pyridine

HRID 269490ノート

反応式

HRID 269490 の反応式
Br[C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8](S(C)(=O)=O)[C:5]2=[N:6][CH:7]=1.[N:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[C:4]3[CH:10]=[CH:9][NH:8][C:5]3=[N:6][CH:7]=2)=[CH:17][CH:16]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 497588975-Bromo-1-(methanesulfonyl)-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 533199325-(4-Pyridinyl)-1H-pyrrolo(2,3-b)pyridine

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 5-bromo-1-methanesulfonyl-1H-pyrrolo[2,3-b]pyridine (140 mg, 0.51 mmol) and 4-pyridinyl boronic acid (125 mg, 1.02 mmol) in DMF (4 mL) was added aqueous Na2CO3 (2M, 1.3 mL, 2.6 mmol). To this suspension was then added PdCl2(dppf) (20 mg, 0.025 mmol) under N2 atmosphere. The flask was then covered with septa, heated at 80° C. for 9 h, and poured into water. The precipitate was collected by filtration, washed with water, and redissolved in MeOH (10 mL). To this Methanol solution was added 6N NaOH solution (2 mL) and the resulting basic reaction mixture was heated at 50° C. for 3 h. After evaporating the MeOH, the aqueous residue was acidified with 6N HCl to pH=2. The precipitate was filtered off and washed with 2N HCl. The acidic filtrate was then neutralized with saturated NaHCO3 solution. The crude product was collected by filtration, washed with water, and dried on the pump for direct use (60 mg, 0.31 mmol). LC/MS: Rt 1.96 mins.; m/e 196.1 (M+H).

後処理

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. dissolutionredissolved in MeOH (10 mL)
  4. additionTo this Methanol solution was added 6N NaOH solution (2 mL)
  5. temperaturethe resulting basic reaction mixture was heated at 50° C. for 3 h
  6. customAfter evaporating the MeOH
  7. filtrationThe precipitate was filtered off
  8. washwashed with 2N HCl
  9. filtrationThe crude product was collected by filtration
  10. washwashed with water
  11. customdried on the pump for direct use (60 mg, 0.31 mmol)

出典と根拠

ORDレコード
ord-b661ba4b4576428eafe887accdb75d8b
出典データセット
uspto-grants-2008_11
特許番号
US07446199B2

反応ノート

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