Benzene → HCID 178505618, compound

HRID 1875438Notes

Reaction equation

HRID 1875438 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][NH2:9].[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]#[CH:18].C(N(CC)CC)C.C1C=CC=CC=1>C(OCC)(=O)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.[Cu]I>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]1[C:2]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[NH:8][N:9]=1

Participants

8

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 6433581-Ethynyl-2-fluorobenzeneHCID 1381941(2-Iodophenyl)hydrazine

Product 1

HCID 178505618HCID 178505618, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Under argon, 200 mg (0.86 mmol) of 2-iodophenylhydrazine, 133 mg (1.11 mmol) of 2-fluoro-phenylacetylene, 30 mg (0.04 mmol) of bis(triphenylphosphine)palladium(II) chloride and 8 mg (0.04 mmol) of copper(I) iodide are introduced into a mixture of 1.5 ml of triethylamine and 3.5 ml of benzene. The mixture is heated to reflux for 4 h and then diluted with ethyl acetate and filtered. The filtrate is concentrated and the residue is purified by preparative HPLC. 36 mg (18% of theory) of the desired product are obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 4 h
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated
  5. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-4e37bd05a0c5484e89543db783f78968
Source dataset
uspto-grants-2012_11
Patent number
US08309551B2

Reaction notes

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