Triphenylphosphine → 3-Bromo-2-(2-but-1-ynyl-5-fluoro-phenoxymethyl)-pyridine

HRID 423183Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423183
[Br:1][C:2]1[C:3]([CH2:8][OH:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:10]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1O)#[C:11][CH2:12][CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>ClCCl>[Br:1][C:2]1[C:3]([CH2:8][O:9][C:19]2[CH:18]=[C:17]([F:20])[CH:16]=[CH:15][C:14]=2[C:10]#[C:11][CH2:12][CH3:13])=[N:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 14022521(3-Bromopyridin-2-yl)methanolHCID 595651802-But-1-ynyl-5-fluoro-phenol

Produkt 1

HCID 595651733-Bromo-2-(2-but-1-ynyl-5-fluoro-phenoxymethyl)-pyridineAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (3-bromo-pyridin-2-yl)-methanol (3.09 g, 16.43 mmol), 2-but-1-ynyl-5-fluoro-phenol (2.70 g, 16.43 mmol), and triphenylphosphine (6.46 g, 24.64 mmol) in dichloromethane (162 mL) is cooled to −5 to 0° C. Diisopropyl azodicarboxylate (DIAD) is added (4.85 mL, 24.64 mmol) dropwise over a 15 min period. After 1 h the solvent is evaporated and the crude material directly purified by flash chromatography (SiO2; 4% hexane: AcOEt) to give 3.5 g (64%) of the title compound. LCMS m/e 334 [M+H]+.

Aufarbeitung

  1. customAfter 1 h the solvent is evaporated
  2. customthe crude material directly purified by flash chromatography (SiO2; 4% hexane: AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-d414e0bb315b4f61bfc0d5476d72a26d
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101761B2

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