Triethylamine → HCID 68460100, compound

HRID 1915469Notes

Reaction equation

Br[C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([N+:13]([O-:15])=[O:14])=[CH:5][C:3]=1[NH2:4].CCN(CC)CC.[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])#[CH:24]>C1(C)C=CC=CC=1.O.[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>[N+:13]([C:6]1[C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:2]([C:24]#[C:23][Si:25]([CH3:28])([CH3:27])[CH3:26])=[C:3]([CH:5]=1)[NH2:4])([O-:15])=[O:14]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-bromo-5-nitro-4-(trifluoromethyl)aniline (10.0 g, 35.1 mmol) in toluene/H2O (100 mL, 1:1, v/v) was added CuI (0.4 g, 2.10 mmol), Et3N (9.5 mL, 68.16 mmol), Pd(PPh3)2Cl2 (5.0 g, 7.12 mmol) and ethynyltrimethylsilane (5.2 g, 53 mmol) successively under an atmosphere of nitrogen at room temperature. The reaction mixture was transferred to a sealed pressure flask and heated at 70° C. for 10 h. The reaction mixture was cooled down to room temperature, filtered, evaporated in vacuo and purified by silica gel column chromatography (1 to 20% EtOAc in petroleum ether as eluant) to afford 5-nitro-4-(trifluoromethyl)-2-((trimethylsilyl)ethynyl)aniline (6.0 g, 57%) as yellow solid. 1H NMR (300 MHz, CDCl3): 7.67 (s, 1H), 7.13 (s, 1H), 4.86 (br s, 2H), 0.29 (s, 9H).

Workup

customThe reaction mixture was transferred to a sealed pressure flask
temperatureThe reaction mixture was cooled down to room temperature
filtrationfiltered
customevaporated in vacuo
custompurified by silica gel column chromatography (1 to 20% EtOAc in petroleum ether as eluant)

Sources & evidence

ORD record: ord-358d125d3d284d30bf1984c8a93f72dc
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614327B2

Reaction notes

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