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

HRID 57885노트

반응식

HRID 57885 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
105 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6b78e39db4b440cc8bedf00573524ac8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434725B2

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