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

HRID 57813

反応式

HRID 57813 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 6342Acetonitrile溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-46c1ff7a52d94e9c8438720064bfdcd0
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

関連ノート

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