Toluene → HCID 18331456, compound

HRID 2270548Notes

Reaction equation

HRID 2270548 reaction equation
C(OC([N:8]([CH2:16][C:17]1[CH:18]=[C:19](Br)[CH:20]=[CH:21][CH:22]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=O)(C)(C)C.CC(C)([O-])C.[K+].[NH2:30][C:31]1[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][N:32]=1.C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].O.C(OCC)(=O)C>[C:12]([O:11][C:9]([NH:8][CH2:16][C:17]1[CH:18]=[C:19]([NH:30][C:31]2[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][N:32]=2)[CH:20]=[CH:21][CH:22]=1)=[O:10])([CH3:13])([CH3:14])[CH3:15]

Participants

9

Reactant 4

HCID 1140TolueneHCID 15332-Amino-4-methylpyridineHCID 18331463HCID 18331463, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18331456HCID 18331456, compoundYield 13.8%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 15826098Cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(di-(t-butoxycarbonyl)aminomethyl)bromobenzene (260 mg), tris(dibenzylideneacetone)dipalladium (42 mg), diphenylphosphinoferrocene (50 mg), potassium t-butoxide (102 mg), 2-amino-4-methylpyridine (108 mg) and toluene (10 ml) was heated under a nitrogen atmosphere at 80° C. for 22 h. Ethyl acetate and water were added to the reaction mixture. 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:n-hexane=1:1) to give 29.2 mg of the titled compound (yield, 10%).

Workup

  1. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  2. dry with materialdried with anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-31a84c6f11cd44259832916072e8118e
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

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