Sodium Carbonate → 1-(6-Fluoro-2-pyridyl)-6-(5-isopropenyl-3-pyridyl)pyrazolo[4,3-c]pyridine

HRID 57813

반응식

HRID 57813 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[N:12]=3)[C:4]=2[CH:3]=1.[C:18]([C:21]1[CH:22]=[N:23][CH:24]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:26]=1)([CH3:20])=[CH2:19].O.C([O-])(=O)C.[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)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].ClCCl>[F:17][C:13]1[N:12]=[C:11]([N:10]2[C:4]3[CH:3]=[C:2]([C:25]4[CH:24]=[N:23][CH:22]=[C:21]([C:18]([CH3:20])=[CH2:19])[CH:26]=4)[N:7]=[CH:6][C:5]=3[CH:8]=[N:9]2)[CH:16]=[CH:15][CH:14]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 23702041Potassium acetate hydrateHCID 862802436-Chloro-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridineHCID 867070193-(Prop-1-en-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine

생성물 1

HCID 867070211-(6-Fluoro-2-pyridyl)-6-(5-isopropenyl-3-pyridyl)pyrazolo[4,3-c]pyridine

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 6342Acetonitrile용매

반응 조건

온도
150 °C

실험 절차

A mixture of 6-chloro-1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridine (1.759 mmol; 437.3 mg), 3-isopropenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.638 mmol; 646.6 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.1759 mmol; 147 mg), potassium acetate hydrate (2.638 mmol; 1.3 mL) and sodium carbonate (2.638 mmol; 1.3 mL) in Acetonitrile (10 mL) in a pressure tube was heated under microwave at 150° C. for 5 min. The mixture was cooled to room temperature. The layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layer was concentrated. The residue was purified on silica eluted with 0 to 6% MeOH in DCM to afford 1-(6-fluoro-2-pyridyl)-6-(5-isopropenyl-3-pyridyl)pyrazolo[4,3-c]pyridine.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with EtOAc
  4. concentrationThe combined organic layer was concentrated
  5. customThe residue was purified on silica
  6. washeluted with 0 to 6% MeOH in DCM

출처 및 근거

ORD 기록
ord-46c1ff7a52d94e9c8438720064bfdcd0
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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