ethyl N-ethoxycarbonyliminocarbamate → HCID 59418762, compound

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([OH:12])=[CH:4][CH:3]=1.[CH3:13][N:14]([CH3:25])[C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][CH:24]=1)[O:18][CH2:19][CH2:20]O.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[Br:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][CH2:20][CH2:19][O:18][C:17]2[CH:22]=[CH:23][CH:24]=[C:15]([N:14]([CH3:13])[CH3:25])[CH:16]=2)=[CH:4][CH:3]=1

Participants

Procedure

Polystyrene bound PPh3 (0.77 g at 1 mmol/g, 0.77 mmol, 1.5 eq) was added to a solution of methyl 6-bromo-3-hydroxypicolinate (0.119 g, 0.51 mmol) and 2-(3-(dimethylamino)phenoxy)ethanol (39B) (0.093 g, 0.51 mmol) in dry DCM (5 mL). To this was added diethyl azodicarboxylate (0.134 mg, 0.77 mmol) dropwise, and the reaction mixture was stirred at rt for 4 hours, filtered to remove the resin, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with a gradient of PE:EtOAc 75:25-60:40, to provide the desired product methyl 6-bromo-3-(2-(3-(dimethylamino)phenoxy)ethoxy)picolinate (39C).