Triethylamine → HCID 86682993, compound

HRID 1497155Notes

Reaction equation

HRID 1497155 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C#C[Si](C)(C)C)=[CH:4][CH:3]=1.[CH2:15](N(CC)CC)[CH3:16].Br[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][C:30]([F:33])([F:32])[F:31].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[Cu]I>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[C:6]([C:15]#[C:16][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][C:30]([F:33])([F:32])[F:31])[CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 27772661-Bromo-2-(trifluoromethoxy)benzeneHCID 86682992HCID 86682992, compound

Product 1

HCID 86682993HCID 86682993, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-chloro-2-trimethylsilanylethynyl-phenylamine (300 mg, 1.34 mmol) in THF (10 ml) was added triethylamine (0.6 ml, 4.02 mmol), and 1-bromo-2-trifluoromethoxy-benzene (0.3 ml, 2.01 mmol). The mixture was purged with argon for 10 min and then PdCl2 (PPh3)2 (47 mg, 0.07 mmol) was added followed by CuI (7.7 mg, 0.04 mmol). The reaction mixture was then heated to 70° C. TBAF (1M solution in THF) (1.54 ml, 1.54 mmol) was added and the reaction mixture was stirred for 1 h at 70° C. After cooling, the mixture was filtered through celite bed, washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography (2-3% ethyl acetate in hexane) to obtain 4-chloro-2-(2-trifluoromethoxy-phenylethynyl)-phenylamine (210 mg, 50% yield) as a brown solid. GC-MS: 311 (M).

Workup

  1. customThe mixture was purged with argon for 10 min
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered through celite bed
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by flash column chromatography (2-3% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8a7c7222d6d1497d8da0b5483f299c4d
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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