2-Dimethylamino-6-vinyl-isonicotinic acid tert-butyl ester → 2-Dimethylamino-6-ethylisonicotinic acid tert-butyl ester

HRID 1908754Notes

Reaction equation

HRID 1908754 reaction equation
[C:1]([O:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([CH:13]=[CH2:14])[N:10]=[C:9]([N:15]([CH3:17])[CH3:16])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[N:10]=[C:9]([N:15]([CH3:16])[CH3:17])[CH:8]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 670269302-Dimethylamino-6-vinyl-isonicotinic acid tert-butyl ester

Product 1

HCID 670269212-Dimethylamino-6-ethylisonicotinic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-dimethylamino-6-vinyl-isonicotinic acid tert-butyl ester (877 mg, 3.53 mmol) in methanol (15 mL), Pd/C (150 mg, 10% Pd) is added and the mixture is stirred under 2 atm of H2 at rt for 3 h. The catalyst is filtered off and the filtrate is evaporated to give crude 2-dimethylamino-6-ethyl-isonicotinic acid tert-butyl ester; LC-MS: tR=0.76 min, [M+1]+=251.10. This material is dissolved in 6 N aq. HCl (60 mL) and the mixture is stirred at 80° C. for 72 h before the solvent is evaporated. The crude product is purified by MPLC on RP-C18-silica gel to give 2-dimethylamino-6-ethyl-isonicotinic acid (332 mg) as an orange oil, LC-MS: tR=0.51 min, [M+1]+=195.10.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-71602873b9bd403799feeb21a918b9c1
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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