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

HRID 57885ノート

反応式

HRID 57885 の反応式
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:13]=[CH:12][C:11]3[CH:14]=[N:15][NH:16][C:10]=3[CH:9]=2)[CH:5]=[N:4][CH:3]=1.Br[C:18]1[N:23]=[C:22]([F:24])[C:21]([Cl:25])=[CH:20][CH:19]=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:25][C:21]1[CH:20]=[CH:19][C:18]([N:16]2[C:10]3[CH:9]=[C:8]([C:6]4[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[N:7]=4)[N:13]=[CH:12][C:11]=3[CH:14]=[N:15]2)=[N:23][C:22]=1[F:24]

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 867070806-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine

生成物 1

HCID 867070791-(5-Chloro-6-fluoro-2-pyridyl)-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine収率 48.1%

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
105 °C

実験手順

To a mixture of 6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine (1.325 mmol; 279.9 mg) and 6-bromo-3-chloro-2-fluoro-pyridine (1.988 mmol; 418.3 mg) in 1,4-Dioxane (10 mL) under Argon was added cesium carbonate (3.975 mmol; 1295 mg), Xantphos (0.2253 mmol; 130.4 mg), and tris(dibenzylideneacetone)dipalladium(0) (0.1325 mmol; 121.3 mg). The resulting mixture was sealed in a pressure tube and heated at 105° C. overnight. 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-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine (217.1 mg, 48%).

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-6b78e39db4b440cc8bedf00573524ac8
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

反応ノート

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