HCID 25105097, compound → HCID 66624791, compound

HRID 1629673Notes

Reaction equation

HRID 1629673 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](Br)=[CH:11][CH:12]=2)[CH:7]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:6][CH:5]1[CH3:23])(=[O:3])[CH3:2].[CH3:24][C:25]1[N:26]([CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[C:27]([Sn](CCCC)(CCCC)CCCC)=[CH:28][N:29]=1>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:27]3[N:26]([CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[C:25]([CH3:24])=[N:29][CH:28]=3)=[CH:11][CH:12]=2)[CH:7]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:6][CH:5]1[CH3:23])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 25105097HCID 25105097, compoundHCID 25254471HCID 25254471, compound2×

Product 1

HCID 66624791HCID 66624791, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

[Step 1] 44 mg (cis:trans=3:1) of 1-acetyl-6-bromo-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline (compound 74) and 56 mg of 2-methyl-5-(tributylstannyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazole were dissolved in 1 mL of DMF, and 6 mg of tetrakis(triphenylphosphine)palladium was added to the solution. The mixture was stirred in a sealed tube for 12 hours at 120° C. After completion of the reaction, DMF was distilled off under reduced pressure. The resulting residue was dissolved in ethyl acetate, and then the solution was filtered through Celite to remove any insoluble materials. The ethyl acetate solution was washed with water, dehydrated over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (ethyl acetate:aqueous ammonia=1:0.01). Thus, 31 mg (cis:trans=3:1, yield 53%) of 1-acetyl-6-{2-methyl-1-[[2-(trimethylsilyl)ethoxy]methyl]-1 H-imidazol-5-yl}-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydroquinoline was obtained as a brown oily substance.

Workup

  1. distillationwas distilled off under reduced pressure
  2. dissolutionThe resulting residue was dissolved in ethyl acetate
  3. filtrationthe solution was filtered through Celite
  4. customto remove any insoluble materials
  5. washThe ethyl acetate solution was washed with water
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified

Sources & evidence

ORD record
ord-2d7ec30f49254c469ceceeeb579079b9
Source dataset
uspto-grants-2014_07
Patent number
US08791090B2

Reaction notes

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