Formic Acid → HCID 86686016, Verbindung

HRID 2277721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2277721
[N:1]1([C:6](=[O:8])[CH3:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.[Br:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14](I)[CH:15]=1.C(N(CC)CC)C.C(O)=O>CN(C=O)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.O>[Br:9][C:10]1[CH:15]=[C:14]([CH:3]2[CH2:4][CH2:5][N:1]([C:6](=[O:8])[CH3:7])[CH2:2]2)[CH:13]=[N:12][CH:11]=1

Komponenten

8

Edukt 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 8204093-Bromo-5-iodopyridineHCID 11446304HCID 11446304, Verbindung

Produkt 1

HCID 86686016HCID 86686016, VerbindungAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 1-(2,5-dihydro-pyrrol-1-yl)-ethanone (70 mg, 0.63 mmol), 3-bromo-5-iodo-pyridine (283 mg, 1 mmol), triethyl amine (130 mg, 1.26 mmol), formic acid (41 mg, 0.88 mmol) and tetrakis(triphenylphosphine)palladium(0) (72.8 mg, 0.063 mmol) in DMF (3 mL) was stirred for 24 hours at 90° C. under nitrogen. After cooling to room temperature, the mixture was treated with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate. After removal of solvents, the residue was purified by flash chromatography to afford the title compound as yellowish oil (25 mg, 15%). MS: 269.1 (M+H+).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customAfter removal of solvents
  5. customthe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d5c47487d45e47ec857c09928f7089f4
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133158B2

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