Tricyclohexylphosphine → 6-[1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridin-6-yl]-N-[(4-methoxyphenyl)methyl]pyrazin-2-amine

HRID 57961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57961
Br[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=[N:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:23]1[N:28]=[CH:27][C:26]2[CH:29]=[N:30][N:31]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[N:33]=3)[C:25]=2[CH:24]=1)CCC.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>CN(C)C(=O)C.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]>[F:38][C:34]1[N:33]=[C:32]([N:31]2[C:25]3[CH:24]=[C:23]([C:2]4[N:7]=[C:6]([NH:8][CH2:9][C:10]5[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=5)[CH:5]=[N:4][CH:3]=4)[N:28]=[CH:27][C:26]=3[CH:29]=[N:30]2)[CH:37]=[CH:36][CH:35]=1

Komponenten

6

Edukt 3

HCID 75806TricyclohexylphosphineHCID 867071426-bromo-N-[(4-methoxyphenyl)methyl]pyrazin-2-amineHCID 86707144Tributyl-[1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridin-6-yl]stannane

Produkt 1

HCID 867071436-[1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridin-6-yl]-N-[(4-methoxyphenyl)methyl]pyrazin-2-amineAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 6-bromo-N-[(4-methoxyphenyl)methyl]pyrazin-2-amine (0.9932 mmol; 768.8 mg), tributyl-[1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridin-6-yl]stannane (2.173 mmol; 1093 mg), tricyclohexylphosphine (0.1192 mmol; 33.42 mg) and Tris(dibenzylideneacetone)dipalladium (0) (0.04966 mmol; 45.47 mg) in N,N-Dimethylacetamide (15 mL) was purged with Argon for 1 min. The reaction mixture was sealed and heated at 150° C. under microwave for 45 min. The mixture was partitioned between EtOAc and water. The organic layer was concentrated and the residue was purified on silica eluted with 0 to 100% EtOAc in Heptane to afford 6-[1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridin-6-yl]-N-[(4-methoxyphenyl)methyl]pyrazin-2-amine (316.3 mg, 48%).

Aufarbeitung

  1. customwas purged with Argon for 1 min
  2. customThe reaction mixture was sealed
  3. customThe mixture was partitioned between EtOAc and water
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified on silica
  6. washeluted with 0 to 100% EtOAc in Heptane

Quellen und Nachweise

ORD-Eintrag
ord-85d3b572cb67465e9add09c7c5801774
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434725B2

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