Chloroform → HCID 44193184, compound

HRID 2421250Notes

Reaction equation

HRID 2421250 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[C:24]3[C:19](=[C:20]([O:25]CC4C=CC=CC=4)[CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)[CH:5]=[CH:6][C:7]=1[O:8]CC1C=CC=CC=1.C(Cl)(Cl)Cl.CCCCCC.N1C2C(=CC=CC=2)CC1>C(O)C.C(OCC)(=O)C.CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([OH:25])[C:19]=3[CH:18]=[CH:17]2)[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

9

Reactant 4

HCID 6212ChloroformHCID 8058HexaneHCID 10328IndolineHCID 59627929HCID 59627929, compound

Product 1

HCID 44193184HCID 44193184, compoundYield 67.9%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-4-[(phenylmethyl)oxy]-1H-indole (D1) (2.32 g, 5.48 mmol) in ethanol (100 mL) and ethyl acetate (100 mL) was hydrogenated in the presence of 10% Pd on charcoal (500 mg) at atmospheric pressure and room temperature overnight. The mixture was filtered and concentrated and then purified by chromatography on silica gel (elution with 0-50% ethyl acetate in hexane) to give a pink gum, which was solidified by the addition of chloroform (˜0.5 mL) and hexane. The product was collected by filtration and washed with hexane to give an off white powder. This product was dissolved in methanol and passed through an SCX cartridge (to trap a trace of indoline formed in the reaction) and the cartridge was eluted with methanol. The product containing fractions were concentrated and then triturated with hexane and dried to give the title compound (E1) as an off-white solid (905 mg).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. custompurified by chromatography on silica gel (elution with 0-50% ethyl acetate in hexane)
  4. customto give a pink gum, which
  5. filtrationThe product was collected by filtration
  6. washwashed with hexane
  7. customto give an off white powder
  8. customformed in the reaction) and the cartridge
  9. washwas eluted with methanol
  10. additionThe product containing fractions
  11. concentrationwere concentrated
  12. customtriturated with hexane
  13. customdried

Sources & evidence

ORD record
ord-1dc6ebfdfcdb47d8ae74fc5d4bed946f
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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