2-(2-Methylpropenyl)-6-vinylisonicotinic acid tert-butyl ester → 2-Ethyl-6-isobutylisonicotinic acid tert-butyl ester

HRID 1908732Notes

Reaction equation

HRID 1908732 reaction equation
[C:1]([O:5][C:6](=[O:19])[C:7]1[CH:12]=[C:11]([CH:13]=[CH2:14])[N:10]=[C:9]([CH:15]=[C:16]([CH3:18])[CH3:17])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:19])[C:7]1[CH:8]=[C:9]([CH2:15][CH:16]([CH3:17])[CH3:18])[N:10]=[C:11]([CH2:13][CH3:14])[CH:12]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 670271162-(2-Methylpropenyl)-6-vinylisonicotinic acid tert-butyl ester

Product 1

HCID 670271142-Ethyl-6-isobutylisonicotinic acid tert-butyl esterYield 86.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the above 2-(2-methyl-propenyl)-6-vinyl-isonicotinic acid tert-butyl ester (444 mg, 1.71 mmol) in methanol (15 mL), Pd/C (50 mg, 10% Pd) is added and the mixture is stirred under 1 atm of H2 at rt for 15 h. The catalyst is filtered off and the filtrate is evaporated. The remaining residue is purified by CC on silica gel eluting with heptane:EA 5:1 to give 2-ethyl-6-isobutyl-isonicotinic acid tert-butyl ester (391 mg) as a colourless oil; LC-MS: tR=1.15 min, [M+1]+=264.11.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe remaining residue is purified by CC on silica gel eluting with heptane:EA 5:1

Sources & evidence

ORD record
ord-6569e3b40f0f4daa8f1307bf4c89242d
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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