Tetramethyltin → HCID 178422723, compound

HRID 1368560Notes

Reaction equation

HRID 1368560 reaction equation
BrC1[CH:3]=[C:4]2[C:9](=CC=1)[CH:8]=[C:7]([C:12]([C:17]1[N:18]=[CH:19][N:20](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:21]=1)([OH:16])[CH:13]([CH3:15])[CH3:14])[CH:6]=[CH:5]2.C[Sn](C)(C)C.[Cl-].[Li+]>CN(C=O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:20]1[CH:21]=[C:17]([C:12]([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:3][CH:4]=[C:5]([CH3:6])[CH:3]=3)[CH:8]=2)([OH:16])[CH:13]([CH3:15])[CH3:14])[N:18]=[CH:19]1

Participants

7

Reactant 3

HCID 11661TetramethyltinHCID 433294Lithium ChlorideHCID 22018349HCID 22018349, compound

Product 1

HCID 178422723HCID 178422723, compoundYield 318.5%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-(6-Bromonaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (2.0 g), tetramethyltin (0.94 ml), dichlorobis(triphenylphosphine)palladium (70 mg) and lithium chloride (432 mg) were dissolved in DMF (20 ml). The solution was stirred at 80° C. for 17 h. After cooling, the solution was diluted with water and extracted with ethyl acetate. The extract was washed with water and saturated sodium chloride solution, successively, and dried. The solvent was distilled off, and the obtained residue was purified by silica gel chromatography (eluent, hexane:THF=6:1→4:1), and crystallized from isopropyl ether to give the titled compound (1.52 g) as colorless needles.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and saturated sodium chloride solution
  4. customsuccessively, and dried
  5. distillationThe solvent was distilled off
  6. customthe obtained residue was purified by silica gel chromatography (eluent, hexane:THF=6:1→4:1)
  7. customcrystallized from isopropyl ether

Sources & evidence

ORD record
ord-46078537a37c44749dceb198bd735422
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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