Methyl Acrylate → (E)-methyl 3-(3-amino-5-chloropyridin-2-yl)acrylate

HRID 624534

Reaktionsgleichung

Reaktionsgleichung von HRID 624534
[NH2:1][C:2]1[C:3](Br)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.NC1C=C(Cl)C=CC=1CO.C(N(CC)CC)C.[C:27]([O:31][CH3:32])(=[O:30])[CH:28]=[CH2:29]>CN(C=O)C>[NH2:1][C:2]1[C:3](/[CH:29]=[CH:28]/[C:27]([O:31][CH3:32])=[O:30])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Komponenten

6

Edukt 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 27696403-Amino-2-bromo-5-chloropyridineHCID 4134900(2-Amino-4-chlorophenyl)methanol

Produkt 1

HCID 86705409(E)-methyl 3-(3-amino-5-chloropyridin-2-yl)acrylateAusbeute 63,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-amino-2-bromo-5-chloropyridine (2.257 ml, 19.96 mmol), Reactant 2 (0.283 g, 0.399 mmol), triethylamine (3.03 g, 29.9 mmol) and methyl acrylate (3.44 g, 39.9 mmol) in 5 mL of DMF was heated at 145° C. under microwave irradiation for 35 min. The reaction mixture was evaporated to dryness and was loaded to flash column (DCM to DCM/EA=10:1) to give 1.98 g of pure (E)-methyl 3-(3-amino-5-chloropyridin-2-yl)acrylate (2.7 g, 12.70 mmol, 63.6% yield) as a light yellow solid and 820 mg of less pure product. 1H NMR (400 MHz, chloroFORM-d) δ ppm=8.01 (d, J=1.8 Hz, 1 H), 7.72 (d, J=15.1 Hz, 1 H), 7.01 (d, J=2.0 Hz, 1 H), 6.92 (d, J=15.3 Hz, 1 H), 4.02 (br. s., 2 H), 3.81 (s, 3 H).

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-75aa025761c7452189a9547a3f894272
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303028B2

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