Dimethylformamide → methyl 3-(3-bromo-2-oxopyrazin-1(2H)-yl)-4-chlorobenzoate

HRID 337170

Reaktionsgleichung

Reaktionsgleichung von HRID 337170
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N:12]1[CH:17]=[CH:16][NH:15][C:14](=O)[C:13]1=[O:19].CN(C)C=O.C(Br)(=O)C([Br:28])=O>C(Cl)Cl>[Br:28][C:14]1[C:13](=[O:19])[N:12]([C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=2[Cl:1])[C:6]([O:8][CH3:9])=[O:7])[CH:17]=[CH:16][N:15]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 84841Ethanedioyl dibromideHCID 66690376methyl 4-chloro-3-(2,3-dioxo-3,4-dihydropyrazin-1(2H)-yl)benzoate

Produkt 1

HCID 66689444methyl 3-(3-bromo-2-oxopyrazin-1(2H)-yl)-4-chlorobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A suspension of methyl 4-chloro-3-(2,3-dioxo-3,4-dihydropyrazin-1(2H)-yl)benzoate (Example 330d, 8 g) in DCM (80 mL) was treated with N,N-dimethylformamide (0.220 mL) and oxalyl bromide (2.94 mL) dropwise over 5 min at room temperature under nitrogen. The resulting mixture was stirred at 20° C. for 16 h. The reaction mixture turned black and was evaporated to afford crude product. Purification (SiO2 chromatography eluting with 30% diethyl ether in dichloromethane) gave the subtitle compound (6.33 g).

Aufarbeitung

  1. customwas evaporated
  2. customto afford crude product
  3. customPurification (SiO2 chromatography eluting with 30% diethyl ether in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-271e63ae36d64fd78b65832e5789dbc4
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889692B2

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