Toluene → HCID 18331429, compound

HRID 2270547Notes

Reaction equation

HRID 2270547 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[N:32]=1.C1(C)C=CC=CC=1>O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([CH2:16][C:17]1[CH:18]=[C:19]([NH:20][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[N:32]=2)[CH:21]=[CH:22][CH:23]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 870092-Chloro-6-methoxypyridineHCID 18331424HCID 18331424, compound

Product 1

HCID 18331429HCID 18331429, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(di-(t-butoxycarbonyl)aminomethyl)aniline (50 mg), tetrakistriphenylphosphine palladium (18 mg), potassium carbonate (24 mg), 2-chloro-6-methoxypyridine (25 mg) and toluene (3 ml) was heated under reflux under nitrogen atmosphere for 16 h and, thereafter, ethyl acetate and water were added. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane=1:4) to give 54.5 mg of the titled compound (yield, 82%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen atmosphere for 16 h
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-043008807cd24e34b51b1b6c6c61f76e
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

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