Tetrahydrofuran → 2-Iodo-3-(2-thiophen-3-ylethoxy)-pyridine

HRID 84408

Reaktionsgleichung

Reaktionsgleichung von HRID 84408
[I:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[S:9]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]O)=[CH:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[I:1][C:2]1[C:7]([O:8][CH2:15][CH2:14][C:11]2[CH:12]=[CH:13][S:9][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 83731Thiophene-3-ethanolHCID 971792-Iodopyridin-3-ol

Produkt 1

HCID 579003112-Iodo-3-(2-thiophen-3-ylethoxy)-pyridineAusbeute 90 %

Versuchsvorschrift

To a solution containing 2-iodo-3-hydroxypyridine 12 (1.85 g, 8.37 mmol), 2-(3-thienyl)ethanol (1.20 mL, 10.9 mmol), and triphenylphosphine (2.85 g, 10.9 mmol) in tetrahydrofuran (46.2 mL, 5.70 mmol) was added diisopropyl azodicarboxylate (2.14 mL, 10.9 mmol) dropwise. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated and purified by flash chromatography EtOAc/Hex (0-100%) eluted at 30% to give 13 (yield 90%). MS: (ESI+) 332.2

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash chromatography EtOAc/Hex (0-100%)
  3. washeluted at 30%

Quellen und Nachweise

ORD-Eintrag
ord-91872510c7d44d4abefa50098bab201c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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