Tetrahydrofuran → Methyl 6-iodo-5-(2-(thiophen-3-yl)ethoxy)nicotinate

HRID 1949848Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1949848
[OH:1][C:2]1[C:3]([I:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O-:9])=[O:8].[S:12]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18]O)=[CH:13]1.[C:20]1(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:11][C:3]1[C:2]([O:1][CH2:18][CH2:17][C:14]2[CH:15]=[CH:16][S:12][CH:13]=2)=[CH:10][C:6]([C:7]([O:9][CH3:20])=[O:8])=[CH:5][N:4]=1

Komponenten

6

Edukt 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 83731Thiophene-3-ethanolHCID 178524761HCID 178524761, Verbindung

Produkt 1

HCID 57900415Methyl 6-iodo-5-(2-(thiophen-3-yl)ethoxy)nicotinateAusbeute 93,2 %

Versuchsvorschrift

To a solution containing 5-hydroxy-6-iodonicotinate (3.70 g, 13.3 mmol), 2-(3-thienyl)ethanol (1.90 mL, 17.2 mmol), and triphenylphosphine (4.52 g, 17.2 mmol) in tetrahydrofuran (73.3 mL, 903 mmol) was added Diisopropyl azodicarboxylate (3.39 mL, 17.2 mmol) dropwise. The reaction mixture was stirred at RT o/n. The reaction mixture was concentrated and purified by flash chromatography EtOAc/Hex (0-100%) (eluted at 30%) to give methyl 6-iodo-5-(2-(thiophen-3-yl)ethoxy)nicotinate (93.2% yield). MS: (ESI+) 390.1

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1514445b91644469be701e9b5c9c10f8
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399690B2

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