Phenothiazine → HCID 10330965, compound

HRID 1769882Notes

Reaction equation

HRID 1769882 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C1C2NC3C(=CC=CC=3)SC=2C=CC=1.[C:25]1([C:31]#[CH:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(N(CC)CC)C.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>[C:25]1([C:31]#[C:32][C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[CH:7][NH:8]3)=[CH:4][CH:3]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 7108PhenothiazineHCID 10821PhenylacetyleneHCID 6764936-Bromoindole

Product 1

HCID 10330965HCID 10330965, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

6-Bromoindole (3.84 g, 19.6 mmol) was dissolved in triethylamine (40 ml.). A catalytic amount of phenothiazine was added, and the solution was degassed by bubbling argon through it. Phenylacetylene (8.60 mL, 78.3 mmol) was added via syringe. Bis(triphenylphosphine)palladium(II) chloride (0.69 g, 0.98 mmol) was added, and the reaction mixture was heated at 75°-85° C. for 5 hours. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo. The crude material was purified by chromatography on silica gel to give 6-phenylethynylindole (2.55 g, 60%).

Workup

  1. customthe solution was degassed
  2. customby bubbling argon through it
  3. temperaturethe reaction mixture was heated at 75°-85° C. for 5 hours
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe crude material was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-436d020d85fa4f9c878b07b555b37a20
Source dataset
uspto-grants-1995_01
Patent number
US05382670

Reaction notes

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