Triethylamine → HCID 178474492, compound

HRID 588585Notes

Reaction equation

HRID 588585 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.I[C:17]1[C:18]([C:26]([F:29])([F:28])[F:27])=[N:19][NH:20][C:21]=1[NH:22][C:23](=[O:25])[CH3:24]>CN(C=O)C.[Cu]I.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:1]1([C:7]#[C:8][C:17]2[C:18]([C:26]([F:28])([F:29])[F:27])=[N:19][NH:20][C:21]=2[NH:22][C:23](=[O:25])[CH3:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 178474493HCID 178474493, compound

Product 1

HCID 178474492HCID 178474492, compoundYield 73.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A degassed solution of phenylacetylene (3.9 ml, 35 mmol) and Et3N (36 mL) in DMF (13.5 mL) was added to N-[4-iodo-3-(trifluoromethyl)-1H-pyrazol-5-yl]acetamide (4.5 g, 14 mmol), CuI (530 mg, 2.8 mmol) and PdCl2(PPh3)2 (980 mg, 1.4 mmol) under an atmosphere of N2. The reaction was then heated to 85° C. for 3.5 h. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography (silica gel, ethyl acetate/isohexane 1:9 to 1:0) yielding the title compound as a brown oil (3 g) which was used in the subsequent step.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by column chromatography (silica gel, ethyl acetate/isohexane 1:9 to 1:0)

Sources & evidence

ORD record
ord-610dd52908984e65a4a87b2bde01cdf0
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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