Triethylamine → 3-(6-Amino-pyridin-3-yl)-acrylic acid tert-butyl ester

HRID 850606

Reaktionsgleichung

Reaktionsgleichung von HRID 850606
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[C:9]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])[CH:10]=[CH2:11].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CC#N.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:14]([O:13][C:9](=[O:12])[CH:10]=[CH:11][C:5]1[CH:4]=[N:3][C:2]([NH2:1])=[CH:7][CH:6]=1)([CH3:17])([CH3:16])[CH3:15]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 706222-Amino-5-bromopyridineHCID 80271Tri-o-tolylphosphine

Produkt 1

HCID 536654623-(6-Amino-pyridin-3-yl)-acrylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 2-amino-5-bromo-pyridine (9-1) (10 g, 58 mmol), tert-butyl acrylate (50 mL, 344 mmol), triethylamine (50 mL, 359 mmol), tri-o-tolylphosphine (3.0 g, 9.8 mmol) and Pd(OAc)2 (1.0 g, 4.5 mmol) in 150 mL CH3CN was purged with argon for 5 min and subsequently refluxed at 110° C. for 20 hr. The mixture was then cooled and concentrated. The residue was purified using silica gel flash chromatography (EtOAc/hexanes 1:1) to afford the desired product 9-2 as a solid.

Aufarbeitung

  1. customwas purged with argon for 5 min
  2. temperatureThe mixture was then cooled
  3. concentrationconcentrated
  4. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-baaac8e461f54ed0ab71fd1ad743c459
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06017926

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