Cesium carbonate → 1-(5-Chloro-6-fluoro-2-pyridyl)-6-(5-ethyl-3-pyridyl)pyrazolo[4,3-c]pyridine

HRID 57829ノート

反応式

HRID 57829 の反応式
[CH2:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[CH:13][C:12]3[CH:15]=[N:16][NH:17][C:11]=3[CH:10]=2)[CH:6]=[N:7][CH:8]=1)[CH3:2].Br[C:19]1[N:24]=[C:23]([F:25])[C:22]([Cl:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:26][C:22]1[CH:21]=[CH:20][C:19]([N:17]2[C:11]3[CH:10]=[C:9]([C:5]4[CH:6]=[N:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=4)[N:14]=[CH:13][C:12]=3[CH:15]=[N:16]2)=[N:24][C:23]=1[F:25]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 722139976-Bromo-3-chloro-2-fluoropyridineHCID 867070346-(5-ethyl-3-pyridyl)-1H-pyrazolo[4,3-c]pyridine

生成物 1

HCID 867070351-(5-Chloro-6-fluoro-2-pyridyl)-6-(5-ethyl-3-pyridyl)pyrazolo[4,3-c]pyridine収率 59%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of the aforesaid 6-(5-ethyl-3-pyridyl)-1H-pyrazolo[4,3-c]pyridine (0.264 mmol; 95.9 mg) and 6-bromo-3-chloro-2-fluoro-pyridine (0.396 mmol; 83.4 mg) in 1,4-Dioxane (10 mL) under Nitrogen was added cesium carbonate (0.528 mmol; 172 mg), Xantphos (0.0449 mmol; 26.0 mg), and Tris(dibenzylideneacetone)dipalladium(0) (0.0264 mmol; 24.2 mg). The resulting mixture was sealed in a pressure tube and heated at 100° C. for 17 hours. The reaction mixture cooled to room temperature, and filtered through Celite. The filter cake was washed with DCM. The filtrate was concentrated. The residue was purified on silica eluted with 0 to 6% MeOH in DCM to afford 1-(5-chloro-6-fluoro-2-pyridyl)-6-(5-ethyl-3-pyridyl)pyrazolo[4,3-c]pyridine (54.9 mg, 59%).

後処理

  1. customThe resulting mixture was sealed in a pressure tube
  2. temperatureThe reaction mixture cooled to room temperature
  3. filtrationfiltered through Celite
  4. washThe filter cake was washed with DCM
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified on silica
  7. washeluted with 0 to 6% MeOH in DCM

出典と根拠

ORDレコード
ord-e61fd45c90244b84aef708c2849a479e
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

反応ノート

読み込み中…