Potassium Acetate → 3-bromo-1-trityl-1H-pyrazolo[3,4-b]pyridine

HRID 539924ノート

反応式

HRID 539924 の反応式
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8](F)[CH:9]=2)[N:4]([C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1.CC([O-])=O.[K+].CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1>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]>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1

参加物

6

反応物 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 712512553-bromo-5-fluoro-1-trityl-1H-pyrazolo[3,4-b]pyridine

生成物 1

HCID 679755003-bromo-1-trityl-1H-pyrazolo[3,4-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
100 °C

実験手順

A solution of 3-bromo-5-fluoro-1-trityl-pyrazolo[3,4-b]pyridine, 44, (16.86 g, 36.79 mmol), KOAc (10.83 g, 110.4 mmol) and 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (14.01 g, 55.18 mmol) in DMF (250 mL) was degassed under a nitrogen stream for 40 min. To the mixture was added Pd(dppf)2Cl2 (3.00 g, 3.68 mmol). The reaction mixture was heated at 100° C. for 90 minutes. The reaction mixture was filtered through a pad of florisil and celite. The filtrate was diluted with ether and brine. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The product was dried on high vacuum pump 3 days. To the product was added 200 mL Et2O and the mixture was stirred and filtered. The filtrate was concentrated in vacuo. The crude residue was diluted with 150 mL hexanes and the suspension was stirred for 3 hours, filtered and concentrated in vacuo to afford 12.6 g of desired product.

後処理

  1. filtrationThe reaction mixture was filtered through a pad of florisil and celite
  2. additionThe filtrate was diluted with ether and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was dried on high vacuum pump 3 days
  7. additionTo the product was added 200 mL Et2O
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. additionThe crude residue was diluted with 150 mL hexanes
  11. stirringthe suspension was stirred for 3 hours
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-29fe0cd76f9e41ec9231f882338ceefa
出典データセット
uspto-grants-2014_10
特許番号
US08871774B2

反応ノート

読み込み中…