2-Methylpyridine → HCID 86634102, compound

HRID 1810944Notes

Reaction equation

HRID 1810944 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1C.[CH2:8]([O:10][P:11]([CH2:16][CH2:17][CH2:18][Br:19])(=[O:15])[O:12][CH2:13][CH3:14])[CH3:9].[C:20](OCC)(=O)C>CN(C=O)C>[Br-:19].[CH2:8]([O:10][P:11]([CH2:16][CH2:17][CH2:18][N+:1]1[CH:2]=[CH:3][C:4]([CH3:20])=[CH:5][CH:6]=1)([O:12][CH2:13][CH3:14])=[O:15])[CH3:9]

Participants

5

Reactant 3

HCID 79752-MethylpyridineHCID 8857Ethyl AcetateHCID 283500Diethyl (3-bromopropyl)phosphonate

Product 1

HCID 86634102HCID 86634102, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of picoline (0.5 g, 5.4 mmol) and diethyl(3-bromopropyl)-phosphonate (1.54 g, 5.9 mmol) was heated in a pressure tube at 130° C. for 4 hours. The mixture was allowed to cool to room temperature, and the resulting mass was dissolved in DMF (4 ml). The combined mixture was then added drop wise to ethyl acetate (40 ml). An oily residue was obtained which was washed with ethyl acetate (2×40 ml) and dried under vacuum to yield 1.7 g of Compound 3 which was then used without any further purification. The structure of Compound 3 is given below:

Workup

  1. temperatureto cool to room temperature
  2. customAn oily residue was obtained which
  3. washwas washed with ethyl acetate (2×40 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5c9d79a11ef9428faea13ccf5bc58637
Source dataset
uspto-grants-2013_01
Patent number
US08362250B2

Reaction notes

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