Triethylamine → HCID 19821077, compound

HRID 1030870Notes

Reaction equation

HRID 1030870 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.[NH2:20][C:21]1[CH:22]=[C:23]([C:27]#[CH:28])[CH:24]=[CH:25][CH:26]=1>CCOCC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]([F:12])([F:11])[F:10])=[CH:3][C:2]=1[C:28]#[C:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[NH2:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 104682Benzenamine, 3-ethynyl-HCID 1442953-Bromo-4-fluorobenzotrifluoride

Product 1

HCID 19821077HCID 19821077, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 10122028Bis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

A multinecked flash as described in Example 1 was charged with 4.93 g (0.020 mol) of 3-bromo-4-fluorobenzotrifluoride, 75 ml of dried, degassed triethylamine, 2.34 g (0.020 mol) of 3-aminophenylacetylene, 0.06 g (0.08 mmol) of bis(triphenylphosphine) palladium II chloride, 0.118 g (0.45 mmol) of triphenylphosphine, and 0.06 g (0.31 mmol) of cuprous iodide. The reaction mixture was heated at 70° C. for 40 hours at which point gas chromatography showed the reaction to be complete. The product mixture was cooled to room temperature and diluted with 75 ml of ether. Filtration of the insoluble hydrobromide salt followed by concentration of the filtrate gave the crude product (5.5 g, 89%) as an orange liquid. Short path distillation of the crude product under reduced pressure gave 4.05 g (0.014 mol, 70% yield) of the product as a yellow solid.

Workup

  1. customof dried
  2. customthe reaction
  3. temperatureThe product mixture was cooled to room temperature
  4. filtrationFiltration of the insoluble hydrobromide salt
  5. customgave the crude product (5.5 g, 89%) as an orange liquid
  6. distillationShort path distillation of the crude product under reduced pressure

Sources & evidence

ORD record
ord-b4cc5c65f4314569b8af0cd25d027cca
Source dataset
uspto-grants-1992_04
Patent number
US05107026

Reaction notes

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