Oxygen → Tert-butyl 2-(but-3-enylamino)-6-methylisonicotinate

HRID 1432109Notes

Reaction equation

HRID 1432109 reaction equation
O=O.[C:3]([O:7][C:8](=[O:17])[C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11](Cl)[CH:10]=1)([CH3:6])([CH3:5])[CH3:4].[CH2:18]([NH2:22])[CH2:19][CH:20]=[CH2:21]>C1(C)C=CC=CC=1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:3]([O:7][C:8](=[O:17])[C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([NH:22][CH2:18][CH2:19][CH:20]=[CH2:21])[CH:10]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

7

Reactant 3

HCID 977OxygenHCID 4437323-Buten-1-amineHCID 860403662-Chloro-6-methyl-isonicotinic acid tert-butyl ester

Product 1

HCID 68545468Tert-butyl 2-(but-3-enylamino)-6-methylisonicotinate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Under rigorous exclusion of oxygen a mixture of 200 mg (0.88 mmol) 2-chloro-6-methyl-isonicotinic acid tert-butyl ester, 10 mg palladium(II)acetate (0.044 mmol), 27 mg (0.44 mol) BINAP (R(+)-2,2-bis(diphenylphosphino)-1,1-binaphtalene) and 62 mg (0.88 mmol) but-3-enylamine in 10 ml toluene is heated at 60° C. for 4 h. The mixture is diluted with EtOAc, washed with 10% aqueous NaHCO3 and water, dried with sodium sulfate and evaporated. Chromatography of the product on silica gel (hexane/EtOAc 9:1) yields the title compound.

Workup

  1. washwashed with 10% aqueous NaHCO3 and water
  2. dry with materialdried with sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-d15b92506bb348ecaa7e92541511aab2
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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