Lithium Chloride → 1-[3-(7-Acetyl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea

HRID 536296

Reaktionsgleichung

Reaktionsgleichung von HRID 536296
Cl[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13]([NH:17][C:18]([NH:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1.C([Sn](CCCC)(CCCC)[C:31]([O:33]CC)=[CH2:32])CCC.[Cl-].[Li+]>C(#N)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:31]([C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:12]=[C:13]([NH:17][C:18]([NH:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1)(=[O:33])[CH3:32]

Komponenten

6

Edukt 3

HCID 433294Lithium ChlorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 574976981-(3-(7-Chloroimidazo[1,2-a]pyridin-3-yl)phenyl)-3-(2,2,2-trifluoroethyl)urea

Produkt 1

HCID 252640271-[3-(7-Acetyl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a suspension of 1-[3-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea (0.1 g, 0.27 mmol), tributyl-(1-ethoxy-vinyl)-stannane (0.091 ml, 0.27 mmol, 1 equiv), lithium chloride (0.034 g, 0.81 mmol, 3 equiv) in acetonitrile (4 ml) was added tetrakis(triphenylphosphine)palladium(0) (0.031 g, 27.2 μmol, 0.1 equiv). The reaction mixture was degassed by bubbling through N2, heated in the microwave at 150° C. for 20 min and filtered through a glass microfibre filter. To the filtrate was added 2N HCl (3 ml) and the mixture stirred vigorously for 2 h at room temperature, neutralised with saturated aqueous NaHCO3, extracted with CH2Cl2, the organics combined dried (MgSO4) and the solvent removed in vacuo. The residue was purified by preparative LC-MS to give the desired product as a yellow solid. MS: [M+H]+ 377

Aufarbeitung

  1. customThe reaction mixture was degassed
  2. customby bubbling through N2
  3. filtrationfiltered through a glass microfibre
  4. filtrationfilter
  5. additionTo the filtrate was added 2N HCl (3 ml)
  6. extractionextracted with CH2Cl2
  7. dry with materialthe organics combined dried (MgSO4)
  8. customthe solvent removed in vacuo
  9. customThe residue was purified by preparative LC-MS

Quellen und Nachweise

ORD-Eintrag
ord-2c05c71a2f31429c99fd0f86db0b9de8
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859583B2

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