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(Pyridin-4-yl)boronic acid → 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (2-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide

HRID 1802252
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1802252
[N:1]1([C:5]([C:7]2[CH:8]=[N:9][N:10]([CH3:25])[C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[C:22](Br)[N:23]=[C:17]3[CH:16]=2)=[O:13])=[O:6])[CH2:4][CH2:3][CH2:2]1.[N:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].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.[Fe+2]>[N:26]1[CH:31]=[CH:30][C:29]([C:22]2[N:23]=[C:17]3[CH:16]=[C:15]([NH:14][C:12]([C:11]4[N:10]([CH3:25])[N:9]=[CH:8][C:7]=4[C:5]([N:1]4[CH2:4][CH2:3][CH2:2]4)=[O:6])=[O:13])[CH:20]=[CH:19][N:18]3[N:21]=2)=[CH:28][CH:27]=1
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Komponenten

6

Edukt 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 573782924-(azetidine-1-carbonyl)-N-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide

Produkt 1

HCID 573783874-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (2-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amideAusbeute 18,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178479796
1,1'-bis(diphenylphosphino)ferrocene palladium (II) chloride dppf
Katalysator
HCID 10340Sodium CarbonateLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Through a mixture of 4-(azetidine-1-carbonyl)-N-(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-1-methyl-1H-pyrazole-5-carboxamide (150 mg, 371 μmol) and pyridin-4-ylboronic acid (68.4 mg, 557 μmol) in dioxane (4 ml) and sat. sodium carbonate solution (1 ml) was bubbled nitrogen for 10 minutes, then 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride/dppf (15.2 mg, 18.6 μmol) was added and the resulting mixture was refluxed for 18 hours under nitrogen atmosphere. The solvent was evaporated and the residue was diluted with ethyl acetate and washed with water, the organic layer was separated, dried over magnesium sulfate, filtrated and evaporated. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using ethyl acetate/methanol 2-5% as eluent affording 4-(azetidine-1-carbonyl)-2-methyl-2H-pyrazole-3-carboxylic acid (2-pyridin-4-yl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-amide (28 mg, 18.8%) as a white solid. mp: >250° C., MS: m/z=403.0 (M+H+)

Aufarbeitung

  1. customwas bubbled nitrogen for 10 minutes
  2. temperaturethe resulting mixture was refluxed for 18 hours under nitrogen atmosphere
  3. customThe solvent was evaporated
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with water
  6. customthe organic layer was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltrated
  9. customevaporated
  10. custompurified by flash chromatography over a 20 g silicagel column

Quellen und Nachweise

ORD-Eintrag
ord-0e0ffa42823a4b31964b185f8ccbb63c
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08349824B2

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