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

HRID 269491ノート

反応式

HRID 269491 の反応式
CS([N:5]1[C:9]2=[N:10][CH:11]=[C:12](B3OC(C)(C)C(C)(C)O3)[CH:13]=[C:8]2[CH:7]=[CH:6]1)(=O)=O.Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=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:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:12]1[CH:13]=[C:8]2[CH:7]=[CH:6][NH:5][C:9]2=[N:10][CH:11]=1

参加物

7

反応物 4

HCID 962WaterHCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 497590461-(Methanesulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 598322245-(2-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 1-methanesulfonyl-5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (300 mg, 0.93 mmol) and 2-bromopyridine (150 mg, 0.95 mmol) in DMF (3 mL) was added aqueous Na2CO3 (2M, 1.9 mL, 3.8 mmol). To this suspension was then added PdCl2(dppf) (60 mg, 0.075 mmol) under N2 atmosphere. The flask was then covered with septa, heated at 80° C. for 9 h, and poured into water (30 mL). The aqueous solution was extracted with ethylacetate (3×30 mL). The combined organic layers were dried over Na2SO4, filtered, and evaporated. The resulting residue was dissolved in MeOH (10 mL) and treated with 6N NaOH solution (2 mL) at 50° C. for 3 h. After evaporating the MeOH, the aqueous residue was acidified with 6N HCl to pH=8. The precipitate was collected by filtration, washed with water, and dried on the pump for direct use (100 mg off-white solid, 0.51 mmol). MS (ES+): m/e=196.1 (M+H); LC: 2.04 min.

後処理

  1. extractionThe aqueous solution was extracted with ethylacetate (3×30 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe resulting residue was dissolved in MeOH (10 mL)
  6. additiontreated with 6N NaOH solution (2 mL) at 50° C. for 3 h
  7. customAfter evaporating the MeOH
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with water
  10. dry with materialdried on the pump for direct use (100 mg off-white solid, 0.51 mmol)
  11. custom2.04 min.

出典と根拠

ORDレコード
ord-77da14bcc6b5489b986090249bb98baf
出典データセット
uspto-grants-2008_11
特許番号
US07446199B2

反応ノート

読み込み中…