Triethylborane → 6-(2,6-Diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester

HRID 251597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 251597
[CH3:1][O:2][C:3](=[O:21])[C:4]1[C:9](Cl)=[CH:8][C:7]([C:11]2[C:16]([CH2:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:19][CH3:20])=[N:6][CH:5]=1.B(CC)(CC)[CH2:23][CH3:24].C([O-])([O-])=O.[Na+].[Na+].CCCCCC>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:21])[C:4]1[C:9]([CH2:23][CH3:24])=[CH:8][C:7]([C:11]2[C:16]([CH2:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:19][CH3:20])=[N:6][CH:5]=1

Komponenten

7

Edukt 4

HCID 7357TriethylboraneHCID 8058HexaneHCID 10340Sodium CarbonateHCID 596781594-Chloro-6-(2,6-diethyl-phenyl)-nicotinic acid methyl ester

Produkt 1

HCID 596783286-(2,6-Diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-chloro-6-(2,6-diethyl-phenyl)-nicotinic acid methyl ester (2.5 g, 8.2 mmol), Et3B (1M in Hexane, 49 mL, 49 mmol), Na2CO3 (2M in H2O, 12.3 mL) and Pd(PPh3)4 (500 mg) in toluene (36 mL) is heated at 80° C. under argon for 2 days. On cooling, hexane (50 mL) is added and the organic layer separated. The organic layer is washed with saturated Na2CO3 and water, dried (Na2SO4), and concentrated. The residue is purified by silica gel chromatography (hexane/EtOAc 4:1) to give 6-(2,6-diethyl-phenyl)-4-ethyl-nicotinic acid methyl ester. 1H NMR (CDCl3) 9.15 (s, 1H), 7.30 (m, 1H), 7.21 (s, 1H), 7.15 (d, 2H), 3.97 (s, 3H), 3.06 (q, 2H), 2.31 (m, 4H), 1.26 (t, 3H), 1.03 (t, 6H).

Aufarbeitung

  1. temperatureOn cooling
  2. customthe organic layer separated
  3. washThe organic layer is washed with saturated Na2CO3 and water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel chromatography (hexane/EtOAc 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-011c08155e794e2e84183dc8ceec273d
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863454B2

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