Lithium Chloride → HCID 178450047, compound

HRID 480458Notes

Reaction equation

HRID 480458 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]([OH:45])([C:21]3[N:22]=[CH:23][N:24](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:25]=3)[CH:18]([CH3:20])[CH3:19])[CH:13]=2)[CH:8]=1)(=O)=O.C([Sn](CCCC)(CCCC)[C:53]1[O:54][CH:55]=[CH:56][CH:57]=1)CCC.[Cl-].[Li+]>CN(C=O)C.O.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>[O:54]1[CH:55]=[CH:56][CH:57]=[C:53]1[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C:17]([C:21]1[N:22]=[CH:23][NH:24][CH:25]=1)([OH:45])[CH:18]([CH3:20])[CH3:19])[CH:11]=[CH:10]2

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 43936882-(Tributylstannyl)furanHCID 222850556-[1-Hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthyl Trifluoromethanesulfonate

Product 1

HCID 178450047HCID 178450047, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

6-[1-Hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthyl trifluoromethanesulfonate (2.0 g), 2-(tributylstannyl)furan (1.26 mL), tetrakis(triphenylphosphine)palladium (115 mg) and lithium chloride (259 mg) were dissolved in DMF (10 mL) and heated at 80 for 4 h. The reaction mixture was diluted with water, extracted with ethyl acetate. The extract was washed with water and brine, dried and concentrated. The residue was purified by column chromatography (eluent; hexane:THF=4:1) and crystallized from ethyl acetate-hexane to give the titled compound (1.48 g) as a colorless powder.

Workup

  1. temperatureheated at 80 for 4 h
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (eluent; hexane:THF=4:1)
  7. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5f911cb8ccd24ed6bef244b5cf9d5262
Source dataset
uspto-grants-2003_11
Patent number
US06649643B1

Reaction notes

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