Water → 6-((8-fluoro-6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)quinolin-3-ol

HRID 40336

Reaktionsgleichung

Reaktionsgleichung von HRID 40336
Cl[C:2]1[CH:3]=[C:4]([F:24])[C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][C:16]([O:22]C)=[CH:15]4)=[N:9][N:10]=2)[CH:7]=1.[CH3:25][N:26]1[CH:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[N:27]1.C([O-])([O-])=O.[Na+].[Na+].O>COCCOC.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].C(Cl)Cl.CS(C)=O>[F:24][C:4]1[C:5]2[N:6]([C:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]=[CH:17][C:16]([OH:22])=[CH:15]4)=[N:9][N:10]=2)[CH:7]=[C:2]([C:29]2[CH:28]=[N:27][N:26]([CH3:25])[CH:30]=2)[CH:3]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 441812536-((6-Chloro-8-fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)-3-methoxyquinoline

Produkt 1

HCID 441811476-((8-fluoro-6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)quinolin-3-olAusbeute 27,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of crude 6-((6-chloro-8-fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)-3-methoxyquinoline (200 mg, 584 μmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (600 mg, 2884 μmol), PdCl2(dppf)-CH2Cl2 adduct (24 mg, 29 μmol), and Na2CO3 (500 mg, 4717 μmol) in DME (7 mL)-H2O (5 mL) was heated at 100° C. under nitrogen. After overnight, the sludge was treated with DMSO (10 mL) and filtered. The DMSO solution was purified on HPLC (10-60%/10 min). The product fraction was concentrated to dryness with toluene. The solid was then triturated with MeOH-hexane (1:2) to give a brown powder (60 mg). LCMS (ESI pos. ion): calc'd for C20H15FN6O: 374.1. found 375.1 (M+1).

Aufarbeitung

  1. filtrationfiltered
  2. customThe DMSO solution was purified on HPLC (10-60%/10 min)
  3. concentrationThe product fraction was concentrated to dryness with toluene
  4. customThe solid was then triturated with MeOH-hexane (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-4b4849fbabb24ce8a12c2fd00689ee17
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524900B2

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