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

HRID 539924노트

반응식

HRID 539924 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 679755003-bromo-1-trityl-1H-pyrazolo[3,4-b]pyridine

시약·촉매·용매 2

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

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-29fe0cd76f9e41ec9231f882338ceefa
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871774B2

반응 노트

불러오는 중…