Water → HCID 23363903, compound

HRID 1081276Notes

Reaction equation

HRID 1081276 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[O:15][CH2:14][CH2:13][O:12]1.[C:16]12[CH2:22][CH:19]([CH2:20][CH2:21]1)[CH2:18][CH:17]=2.N1CCCCC1.O>CN(C=O)C.C(O)=O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[CH:16]12[CH2:22][CH:19]([CH2:20][CH2:21]1)[CH2:18][CH:17]2[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[O:15][CH2:14][CH2:13][O:12]1

Participants

9

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 3099024HCID 3099024, compoundHCID 13129031Bicyclo[2.2.1]hept-1-ene

Product 1

HCID 23363903HCID 23363903, compoundYield 60%

Reagents, catalysts & solvents 4

HCID 178419050HCID 178419050, compoundCatalystHCID 284Formic AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

5'-Iodo-spiro[1,3-dioxolane-2,3'-[3H]indol]-2'(1'H)-one (3.5 g), bicyclo[2.2.1]heptene (1.15 g), piperidine (3.2 g) and bis(triphenylphosphine)palladium (II) acetate (0.35 g) in DMF (5 ml) and formic acid (1.1 ml) were heated and stirred under nitrogen at 60° C. for 1 hour. The mixture was cooled, water (50 ml) and ethyl acetate (50 ml) were added, and after 5 minutes the organic layer was separated, washed, dried and evaporated to dryness. The residue was purified by flash chromatography to yield the title compound (60%).

Workup

  1. temperatureThe mixture was cooled
  2. customafter 5 minutes the organic layer was separated
  3. washwashed
  4. customdried
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4948956204e14d6c81bfa60e1736dc9d
Source dataset
uspto-grants-1996_12
Patent number
US05585378

Reaction notes

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