2-(Tributylstannyl)pyridine → 3-[4-(4-Acetyl-3-hydroxy-2-pyridin-2-yl-phenoxymethyl)-benzyl]-benzoic acid methyl ester

HRID 1717821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1717821
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[C:21]([OH:28])[C:20]=3I)=[CH:13][CH:12]=2)[CH:5]=1.C([Sn](CCCC)(CCCC)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1)CCC>C1(C)C=CC=CC=1.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>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[C:21]([OH:28])[C:20]=3[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)=[CH:13][CH:12]=2)[CH:5]=1

Komponenten

5

Edukt 2

HCID 6077842-(Tributylstannyl)pyridineHCID 666995233-[4-(4-Acetyl-3-hydroxy-2-iodo-phenoxymethyl)-benzyl]-benzoic acid methyl ester

Produkt 1

HCID 1360880293-[4-(4-Acetyl-3-hydroxy-2-pyridin-2-yl-phenoxymethyl)-benzyl]-benzoic acid methyl esterAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3-[4-(4-acetyl-3-hydroxy-2-iodo-phenoxymethyl)-benzyl]-benzoic acid methyl ester (417 mg, 0.808 mmol), 2-tributylstannanyl-pyridine (1.72 g, 4.67 mmol), and tetrakis(triphenylphosphine)palladium(0) (111 mg, 0.096 mmol) in toluene (19 mL) is thoroughly degassed, placed under nitrogen and heated at 100° C. for 16 hours. After cooling to room temperature, the reaction mixture is concentrated in vacuo. The residue thus obtained is purified by flash chromatography (20% to 40% ethylacetate in hexanes) to give 230 mg of the title compound as a yellow oil: MS (m/z): 468 (M+1); 1H NMR (CDCl3) δ 8.74 (m, 1H), 7.87 (m, 2H), 7.78 (m, 2H), 7.56 (d, J=8.0 Hz, 1H), 7.36-7.27 (m, 3H), 7.17 (d, J=8.0 Hz, 2H), 7.11 (d, J=8.0 Hz, 2H), 6.60 (d, J=9.0 Hz, 1H), 5.14 (s, 2H), 3.99 (s, 2H), 3.89 (s, 3H), 2.61 (s, 3H).

Aufarbeitung

  1. customis thoroughly degassed
  2. temperatureAfter cooling to room temperature
  3. concentrationthe reaction mixture is concentrated in vacuo
  4. customThe residue thus obtained
  5. customis purified by flash chromatography (20% to 40% ethylacetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3a40838aa4c04203bea2f4d0b4b674e5
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803938B2

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