Triphenylphosphine → N-(4-(5-chloropent-1-ynyl)phenyl)-2,2,2-trifluoroacetamide

HRID 385259Notes

Reaction equation

HRID 385259 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9](I)=[CH:8][CH:7]=1)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:34][CH2:35][CH2:36][CH2:37][C:38]#[CH:39]>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.[Cu]I>[Cl:34][CH2:35][CH2:36][CH2:37][C:38]#[C:39][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[C:2]([F:14])([F:13])[F:1])=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 843081-Pentyne, 5-chloro-HCID 6869622,2,2-trifluoro-N-(4-iodophenyl)acetamide

Product 1

HCID 57516939N-(4-(5-chloropent-1-ynyl)phenyl)-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 2,2,2-trifluoro-N-(4-iodophenyl)acetamide (3.2 g, 10 mmol, prepared according to Melissaris, A. P. and Litt, M. H. J Org Chem 1994, 59, 5818-5821), dichlorobis(triphenylphosphine)palladium(II) (0.14 g, 0.2 mmol), triphenylphosphine (19 mg, 0.07 mmol), and copper (I) iodide (0.019 g, 0.1 mmol) in triethylamine (50 mL) was degassed under Argon for 10 minutes while stirring in a 55° C. oil bath. The mixture was then treated with 5-chloropentyne (1.1 mL, 10 mmol). After four hours of heating, the mixture was allowed to cool to room temperature and was then filtered through a pad of Celite diatomaceous earth. The filtrate was concentrated under reduced pressure to provide the crude title compound, which was carried forward without further purification. ES/MS calcd. for C14H14ClF3NO+ : 290.1. found m/z=290.1 (M+H)+

Workup

  1. customprepared
  2. temperatureAfter four hours of heating
  3. temperatureto cool to room temperature
  4. filtrationwas then filtered through a pad of Celite diatomaceous earth
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-72c8b6965f65499cbc86575a67196b74
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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