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 1392656Notes

Reaction equation

HRID 1392656 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. 6-(2,6-Diethyl)-4-(3-methoxypropyl)-2-methyl-nicotinic acid ethyl ester: 1H NMR (CDCl3) 7.26 (t, 1H), 7.12 (d, 2H), 7.00 (s, 1H), 4.43 (q, 2H), 3.37 (t, 2H), 3.30 (s, 3H), 2.72 (t, 2H), 2.59 (s, 3H), 2.38-2.25 (m, 4H), 1.92-1.83 (m, 2H), 1.41 (t, 3H), 1.04 (t, 6H). 6-(2,6-Diethyl-phenyl)-2-methyl-4-propyl-nicotinic acid ethyl ester: 1H NMR (CDCl3) 7.25 (t, 1H), 7.18 (d, 2H), 6.99 (s, 1H), 4.43 (q, 2H), 2.62 (q, 2H), 2.60 (s, 3H), 2.38-2.27 (m, 4H), 1.64 (q, 2H), 1.42 (t, 3H), 1.13 (t, 6H), 0.95 (t, 3H).

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-611d8837417f4272bb1d27aa90c8ffad
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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