Potassium Carbonate → 6-(1-Benzyl-pyrrolidin-3-yloxy)-2-methoxy-3-nitro-pyridine

HRID 390290Notes

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

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 6-bromo-2-methoxy-3-nitropyridine (1.5 g, 6.44 mmol), 1-benzyl-pyrrolidin-3-ol (1.14 g, 6.44 mmol) and K2CO3 (0.89 g, 6.44 mmol) in dimethylformamide (DMF) (20 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 380 mg (18.1%) 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-0cb8d58ef8be40e7a6a743ffb86e22ce
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383641B2

Reaction notes

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