Triethylamine → HCID 68460100, compound

HRID 2404866Notes

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): δ 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-cdc49b12be0d4266927e9095e477f846
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802700B2

Reaction notes

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