2-Methyl-4-(tributylstannyl)pyridine → N-[2,3'-Bipyridin]-6'-yl-2',3-dimethyl[2,4'-bipyridine]-5-acetamide

HRID 1036203Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036203
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[N:9][C:10]([NH:13][C:14](=[O:24])[CH2:15][C:16]2[CH:17]=[N:18][C:19](Cl)=[C:20]([CH3:22])[CH:21]=2)=[CH:11][CH:12]=1.[CH3:25][C:26]1[CH:31]=[C:30]([Sn](CCCC)(CCCC)CCCC)[CH:29]=[CH:28][N:27]=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.CN(C=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[N:9][C:10]([NH:13][C:14](=[O:24])[CH2:15][C:16]2[CH:21]=[C:20]([CH3:22])[C:19]([C:30]3[CH:29]=[CH:28][N:27]=[C:26]([CH3:25])[CH:31]=3)=[N:18][CH:17]=2)=[CH:11][CH:12]=1

Komponenten

5

Edukt 2

HCID 216605742-Methyl-4-(tributylstannyl)pyridineHCID 58447789N-(2,3'-bipyridin-6'-yl)-2-(6-chloro-5-methylpyridin-3-yl)acetamide

Produkt 1

HCID 46927131N-[2,3'-Bipyridin]-6'-yl-2',3-dimethyl[2,4'-bipyridine]-5-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
118 °C

Versuchsvorschrift

To a reaction tube were added 5 N-(2,3′-bipyridin-6′-yl)-2-(6-chloro-5-methylpyridin-3-yl)acetamide 124-2 (52 mg, 0.15 mmol), 2-methyl-4-(tributylstannyl)pyridine (115 mg, 0.3 mmol), and Pd(PPh3)4 (35 mg, 0.03 mmol). The tube was subjected to vacuum and back filled with argon. DMF (1.0 ml) was added and the mixture was heated in 118° C. oil bath overnight. After cooled to room temperature, the mixture was filtered through celite, washed and diluted with ethyl acetate (30 ml) and extracted with 0.1 N HCl solution (30 ml). The acidic aqueous phase was treated with Na2CO3 to have pH around 9 and extracted with ethyl acetate (3×20 ml). The combined organic phase was dried over Na2SO4 and concentrated by evaporation. The residue was subjected to silica gel column chromatography with 5% MeOH in DCM as eluent to give N-(2,3′-bipyridin-6′-yl)-2-(2′,3-dimethyl-2,4′-bipyridin-5-yl)acetamide 124 as white solid. MS m/z 396.3 (M+1); 1H NMR 400 MHz (CDCl3) δ 8.93-8.89 (m, 1H), 8.72-8.67 (m, 1H), 8.59 (d, 1H), 8.51 (d, 1H), 8.37-8.29 (m, 2H), 8.23 (bs, 1H), 7.76 (m, 1H), 7.71 (m, 1H), 7.65 (d, 1H), 7.33 (bs, 1H), 7.30-7.24 (m, 1H), 3.81 (s, 2H), 2.63 (s, 3H), 2.38 (s, 3H).

Aufarbeitung

  1. additionback filled with argon
  2. temperatureAfter cooled to room temperature
  3. filtrationthe mixture was filtered through celite
  4. washwashed
  5. additiondiluted with ethyl acetate (30 ml)
  6. extractionextracted with 0.1 N HCl solution (30 ml)
  7. additionThe acidic aqueous phase was treated with Na2CO3
  8. extractionextracted with ethyl acetate (3×20 ml)
  9. dry with materialThe combined organic phase was dried over Na2SO4
  10. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-03a013b89e95463c811892fd3bf4e883
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546396B2

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