Potassium Phosphate, Tribasic → Ethyl 3-amino-6-cyclopropylpicolinate

HRID 467612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 467612
[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8](Br)[N:7]=1)=[O:5])[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P([CH:35]2[CH2:40][CH2:39]CCC2)C2CCCCC2)CCCCC1.C1(B(O)O)CC1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([CH:39]2[CH2:40][CH2:35]2)[N:7]=1)=[O:5])[CH3:2]

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 25137688Ethyl 3-amino-6-bromopicolinate

Produkt 1

HCID 67299907Ethyl 3-amino-6-cyclopropylpicolinate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 3-amino-6-bromo-pyridine-2-carboxylic acid ethyl ester (prepared according to US 2006/199960; 1.0 g, 4.08 mmol), potassium phosphate (3.03 g, 14.3 mmol), tricyclohexylphosphine (0.228 g, 0.82 mmol) and water (1.25 ml) in toluene (25 ml) was added cyclopropylboronic acid (0.91 g, 10.6 mmol) and palladium (II) acetate (90 mg, 0.4 mmol). The resulting suspension was stirred at 100° C. for 24 hours. After solvent evaporation, the title compound was obtained after silica gel chromatography using a heptane/ethyl acetate gradient as yellow solid (0.374 g, 44%).

Aufarbeitung

  1. customAfter solvent evaporation

Quellen und Nachweise

ORD-Eintrag
ord-3ac0d8ec00f04e31b3832a0b80dd3ba3
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623866B2

Notizen zur Reaktion

Wird geladen…