ethyl N-ethoxycarbonyliminocarbamate → HCID 59418762, compound

HRID 2178268Notes

Reaction equation

HRID 2178268 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

5

Reactant 3

HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11344367HCID 11344367, compoundHCID 22175135Methyl 6-bromo-3-hydroxypicolinate

Product 1

HCID 59418762HCID 59418762, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. filtrationfiltered
  2. customto remove the resin
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by column chromatography on silica gel eluting with a gradient of PE

Sources & evidence

ORD record
ord-74a612bb5a02445da6e75cd190f32e07
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

Loading…