Propargyl alcohol → HCID 89924003, Verbindung

HRID 1500938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500938
[Cl:1][C:2]1[CH:14]=[C:13](I)[C:5]([NH:6][CH2:7][CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:4]([F:16])[CH:3]=1.[CH2:17]([OH:20])[C:18]#[CH:19]>CCN(CC)CC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[CH:14]=[C:13]2[C:5](=[C:4]([F:16])[CH:3]=1)[N:6]([CH2:7][CH2:8][S:9]([CH3:12])(=[O:11])=[O:10])[C:18]([CH2:17][OH:20])=[CH:19]2

Komponenten

6

Edukt 2

HCID 7859Propargyl alcoholHCID 899240084-chloro-2-fluoro-6-iodo-N-(2-(methylsulfonyl)ethyl)aniline

Produkt 1

HCID 89924003HCID 89924003, VerbindungAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-2-fluoro-6-iodo-N-(2-(methylsulfonyl)ethyl)aniline (450 mg, 1.2 mmol) and prop-2-yn-1-ol (135 mg, 2.4 mmol) in Et3N (20 ml) was degassed and refluxed under N2 atmosphere. PdCl2(PPh3)2 (90 mg, 0.12 mmol) and CuI (45 mg, 0.24 mmol) were added successively to the reaction mixture. After being stirred under reflux overnight, the mixture was concentrated in vacuo and the residue was poured into water and extracted with EtOAc (50 mL×3). The combined organic layers were dried over Na2SO4 and then concentrated in vacuo. The residue was purified by preparative-TLC (PE: EtOAc=5:1) to give {5-chloro-7-fluoro-1-[2-(methylsulfonyl)ethyl]-1H-indol-2-yl}methanol as a yellow solid (350 mg, yield: 95%).

Aufarbeitung

  1. customwas degassed
  2. temperaturerefluxed under N2 atmosphere
  3. temperatureunder reflux overnight
  4. concentrationthe mixture was concentrated in vacuo
  5. additionthe residue was poured into water
  6. extractionextracted with EtOAc (50 mL×3)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by preparative-TLC (PE: EtOAc=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-1b7f992032a34b73941a164c3a4a477a
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206191B2

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