Toluene → HCID 178526610, compound

HRID 589346Notes

Reaction equation

HRID 589346 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][NH2:9].C1(C)C=CC=CC=1.[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([C:26]#[CH:27])=[CH:22][CH:21]=1)([O-:19])=[O:18]>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(N(CC)CC)C>[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]2[C:2]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[NH:8][N:9]=2)=[CH:22][CH:21]=1)([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 1140TolueneHCID 1367521-Ethynyl-4-nitrobenzeneHCID 1381941(2-Iodophenyl)hydrazine

Product 1

HCID 178526610HCID 178526610, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

Into a dry reaction vessel, 10.3 g (44 mmol) (2-iodophenyl)hydrazine, 100 mL toluene, 50 mL triethylamine, 8.41 g (57.2 mmol) p-nitro phenylacetylene, 500 mg (Ph3P)2PdCl2, 250 mg cuprous iodide were respectively added, and reacted at 110° C. under protection of nitrogen for 4.5 h. It was cooled, rotate evaporated to dryness to remove the solvent, chromatographed on a column to obtain a red liquid 2.15 g (8.50 mmol), at a yield of 19.3%.

Workup

  1. additionwere respectively added
  2. customreacted at 110° C. under protection of nitrogen for 4.5 h
  3. temperatureIt was cooled
  4. customrotate evaporated to dryness
  5. customto remove the solvent
  6. customchromatographed on a column

Sources & evidence

ORD record
ord-7030a05cfa3f4956a6a8400d42f570b2
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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