Diethyl Malonate → 2-(3-Chloro-6-methoxy-[1,5]naphthyridin-4-yl)-acrylic acid ethyl ester
Reaction equation
Br[C:2]1[C:3]([Cl:14])=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2.[C:15](OCC)(=O)[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>>[CH2:20]([O:19][C:17](=[O:18])[C:16]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[N:10]=2)[N:5]=[CH:4][C:3]=1[Cl:14])=[CH2:15])[CH3:21]Participants
3
Procedure
Starting from 8-bromo-7-chloro-2-methoxy-[1,5]naphthyridine (41.75 g, 152.6 mmol) and diethyl malonate (70.2 mL, 3 eq.), the title compound was obtained as a white solid (31.35 g, 107.2 mmol) using the procedures reported in WO 2007/071936 for the analogous methyl ester.
Sources & evidence
- ORD record
- ord-8456a730de8b4b6b9ab8c3ae34722679
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012961B2
Reaction notes
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