Dimethylformamide → N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(pyrimidin-5-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 79464
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:15]=3[C:16]([CH2:31][CH3:32])=[N:17][N:18]4[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=3)=[O:12])=[CH:9][N:10]=[C:4]2[CH:3]=1.CN(C)C=O.[N:38]1[CH:43]=[C:42](B(O)O)[CH:41]=[N:40][CH:39]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.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]>[CH2:31]([C:16]1[C:15]2[C:19](=[CH:20][CH:21]=[CH:22][C:14]=2[NH:13][C:11]([C:8]2[N:5]3[CH:6]=[CH:7][C:2]([C:42]4[CH:43]=[N:38][CH:39]=[N:40][CH:41]=4)=[CH:3][C:4]3=[N:10][CH:9]=2)=[O:12])[N:18]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[N:25]=2)[N:17]=1)[CH3:32]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 672595577-Bromo-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

Produkt 1

HCID 67260638N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(pyrimidin-5-yl)imidazo[1,2-a]pyridine-3-carboxamideAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

7-Bromo-N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (0.06 g, 0.12 mmol) (Example 127) was dissolved in a 1:1 mixture of dimethoxyethane:dimethylformamide (0.6 mL) in a 2 dram vial. Pyrimidin-5-ylboronic acid (0.02 g, 0.18 mmol), PdCl2(dppf)*dcm (0.005 g, 0.006 mmol), and 2 M sodium carbonate solution (0.17 mL, 0.34 mmol) were added. Nitrogen was bubbled through the reaction mixture for 5 minutes before sealing the vial and heating at 90° C. for 16 hours. The reaction mixture was filtered over a 25 mm nylon filter 0.2 μM. The solids were washed with dimethylformamide (1 mL). The filtrate was concentrated under reduced pressure and dried under high vacuum to give N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-(pyrimidin-5-yl)imidazo[1,2-a]pyridine-3-carboxamide (44 mg) as a beige solid. MS (APCI), positive scan, m/z=489.2 (M+H).

Aufarbeitung

  1. customNitrogen was bubbled through the reaction mixture for 5 minutes
  2. filtrationThe reaction mixture was filtered over a 25 mm nylon
  3. filtrationfilter 0.2 μM
  4. washThe solids were washed with dimethylformamide (1 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-252a9c9ae03e445490b64f7da25d7e04
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841455B2

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