6-(2,6-Diethyl-phenyl)-4-(3-methoxy-prop-1-ynyl)-2-methyl-nicotinic acid ethyl ester → 6-(2,6-Diethyl-phenyl)-2-methyl-4-propyl-nicotinic acid ethyl ester

HRID 251624Notes

Reaction equation

HRID 251624 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5]1[C:10]([C:11]#[C:12][CH2:13]OC)=[CH:9][C:8]([C:16]2[C:21]([CH2:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:24][CH3:25])=[N:7][C:6]=1[CH3:26])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:27])[C:5]1[C:10]([CH2:11][CH2:12][CH3:13])=[CH:9][C:8]([C:16]2[C:21]([CH2:22][CH3:23])=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:24][CH3:25])=[N:7][C:6]=1[CH3:26])[CH3:2]

Participants

4

Reactant 1

HCID 669936466-(2,6-Diethyl-phenyl)-4-(3-methoxy-prop-1-ynyl)-2-methyl-nicotinic acid ethyl ester

Product 1

HCID 669941666-(2,6-Diethyl-phenyl)-2-methyl-4-propyl-nicotinic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-(2,6-diethyl-phenyl)-4-(3-methoxy-prop-1-ynyl)-2-methyl-nicotinic acid ethyl ester (160 mg, 0.44 mmol) and 10% Pd/C (40 mg, 25 wt %) in MeOH (20 mL) is hydrogenated for 18 hours at 55 psi (Parr shaker). After filtration through celite, the filtrate is concentrated in vacuo and the residue purified by flash chromatography to give 6-(2,6-diethyl)-4-(3-methoxypropyl)-2-methyl-nicotinic acid ethyl ester and 6-(2,6-diethyl-phenyl)-2-methyl-4-propyl-nicotinic acid ethyl ester.

Workup

  1. filtrationAfter filtration through celite
  2. concentrationthe filtrate is concentrated in vacuo
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-e8b583cdc5854d1280441c68e9eb62b7
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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