Trimethylsilylacetylene → 2,2,2-Trifluoro-N-{2-methyl-5-[(trimethylsilyl)ethynyl]phenyl}acetamide

HRID 1157629Notes

Reaction equation

HRID 1157629 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:15])=[C:6]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:7]=1.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>C1COCC1.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:11][C:10]([F:13])([F:12])[C:9]([NH:8][C:6]1[CH:7]=[C:2]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])[CH:3]=[CH:4][C:5]=1[CH3:15])=[O:14]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 22637059N-(5-bromo-2-methylphenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 595114182,2,2-Trifluoro-N-{2-methyl-5-[(trimethylsilyl)ethynyl]phenyl}acetamideYield 67.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of N-(5-bromo-2-methylphenyl)-2,2,2-trifluoroacetamide (15 g, 54 mmol) in THF (300 mL) was added Pd(PPh3)2Cl2 (3.79 g, 5.4 mmol), CuI (513 mg, 2.7 mmol) and TEA (23 mL, 162 mmol). The solution was heated to 60° C. A solution of trimethylsilylacetylene (11.5 mL, 81 mmol) in THF (200 mL) was added dropwise through an addition funnel over about 60 min. After 16 h, the reaction was concentrated onto silica gel and purified by column chromatography to give the desired product (10.92 g, 67%). 1H NMR (400 MHz, d6-DMSO) δ 10.97 (s, 1H), 7.35-7.30 (m, 3H), 2.18 (S, 3H), 0.21 (s, 9H) ppm.

Workup

  1. concentrationthe reaction was concentrated onto silica gel
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-a8bdf5e0cba14687a84ea6822bdfaf17
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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