ethyl N-ethoxycarbonyliminocarbamate → HCID 59418762, compound

HRID 1641104Notes

Reaction equation

HRID 1641104 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-427e14cfdcf24f399af168856103098f
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Reaction notes

Loading…