Methanol → Methyl 6-pyrrolidinonicotinate

HRID 747792Notes

Reaction equation

HRID 747792 reaction equation
BrC1C=CC([N:8]2[CH2:12]CCC2)=NC=1.[CH3:13][OH:14].[CH2:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[CH3:16].C1(P([C:35]2[CH:40]=[CH:39]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C]=[O:42]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[N:17]1([C:20]2[CH:21]=[CH:39][C:40]([C:35]([O:14][CH3:13])=[O:42])=[CH:12][N:8]=2)[CH2:18][CH2:19][CH2:16][CH2:15]1

Participants

9

Reactant 5

HCID 887MethanolHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 164142265-Bromo-2-(pyrrolidin-1-yl)pyridineHCID 178418416HCID 178418416, compound

Product 1

HCID 2794748Methyl 6-pyrrolidinonicotinate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.6 g (11.1 mmol) of 5-bromo-2-(pyrrolidine-1-yl)pyridine was dissolved in 30 ml of dimethylformamide. 8.9 ml (220 mmol) of methanol, 3.06 ml (22 mmol) of triethylamine, 124 mg (0.5 mmol) of palladium (II) acetate and 2.7 g (11.1 mmol) of triphenylphosphine were added to the solution, and they were stirred in the presence of carbon monoxide at 70° C. overnight. After the treatment with ethyl acetate as the extractant in an ordinary manner, the crude product was obtained, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customwhich was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-a16781bad7bf46de800066aaed260b4c
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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