Cesium carbonate → Diethyl 4-(2,4,6-trimethoxyphenyl)pyridine-2,6-dicarboxylate

HRID 655899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 655899
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[C:4]=1B(O)O.Br[C:17]1[CH:22]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:20]=[C:19]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[C:4]=1[C:17]1[CH:18]=[C:19]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:20]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:22]=1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 41979962,4,6-Trimethoxyphenylboronic acidHCID 13794409Diethyl 4-bromopyridine-2,6-dicarboxylate

Produkt 1

HCID 66814130Diethyl 4-(2,4,6-trimethoxyphenyl)pyridine-2,6-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

2,4,6-trimethoxyphenylboronic acid (2.12 g, 10.0 mmol) and diethyl 4-bromopyridine-2,6-dicarboxylate (3.33 g, 11.0 mmol) were dissolved in dry DMF (50 mL). Caesium carbonate (4.56 g, 14.0 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.23 g, 0.20 mmol) were added, and the mixture was deaerated with argon. The mixture was heated at 95° C. for 48 h. The mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated in vacuo, the residue was dissolved in chloroform (60 mL) and washed with 10% aq. citric acid and water, dried over Na2SO4 and concentrated. Purification was performed on silica gel (eluent petroleum ether bp 40-60° C.; ethyl acetate 5:3→2:5, v/v). Yield was 2.09 g (54%). 1H NMR (CDCl3): δ 1.45 (6H, t, J 7.1); 3.74 (6H, s); 3.90 (3H, s); 4.49 (4H, q, J 7.1); 6.22 (2H, s); 8.28 (2H, s). IR (film)/cm−1 1743, 1610 (C═O); 1339, 1238, 1128 (C—O). ESI-MS: [M+H]+ 390.19 calc. for C20H24NO7+ 390.15.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe residue was dissolved in chloroform (60 mL)
  5. washwashed with 10% aq. citric acid and water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customPurification

Quellen und Nachweise

ORD-Eintrag
ord-a915009a3a7f4ca792d4249967a53347
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071626B2

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