Potassium Carbonate → [2-(6-Methoxy-5-nitro-pyridin-2-yloxy)-ethyl]-propyl-carbamic Acid Tert-Butyl Ester

HRID 390289Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.[C:13]([O:17][C:18](=[O:26])[N:19]([CH2:23][CH2:24][OH:25])[CH2:20][CH2:21][CH3:22])([CH3:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[C:13]([O:17][C:18](=[O:26])[N:19]([CH2:23][CH2:24][O:25][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([O:8][CH3:9])[N:7]=1)[CH2:20][CH2:21][CH3:22])([CH3:14])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 6-bromo-2-methoxy-3-nitropyridine (5 g, 21.46 mmol), (2-hydroxy-ethyl)-propyl-carbamic acid tert-butyl ester (4.36 g, 21.46 mmol) and K2CO3 (2.97 g, 21.46 mmol) in dimethylformamide (DMF) (60 ml) was stirred at room temperature for 24 h and at 40° C. for 4 h. After evaporation of the solvent under reduced pressure the residue was purified by silica gel chromatography with dichloromethane/methanol (10:0; 9:1; 7:3; 0:10) as eluent to provide 2.81 g (36.9%) of the product.

Workup

customAfter evaporation of the solvent under reduced pressure the residue
customwas purified by silica gel chromatography with dichloromethane/methanol (10:0; 9:1; 7:3; 0:10) as eluent

Sources & evidence

ORD record: ord-f7cc1c85bdfd4923899b1fbf4db2e0d3
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383641B2

Reaction notes

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