Trimethylsilylacetylene → HCID 69342593, compound

HRID 855309Notes

Reaction equation

HRID 855309 reaction equation
[F:1][C:2]1[C:3]([C:10]([F:13])([F:12])[F:11])=[CH:4][C:5](I)=[C:6]([CH:8]=1)[NH2:7].[C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])#[CH:15]>C(N(CC)CC)C.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:1][C:2]1[C:3]([C:10]([F:13])([F:12])[F:11])=[CH:4][CH:5]=[C:6]([NH:7][C:15]#[C:14][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:8]=1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 59320603875306-75-5

Product 1

HCID 69342593HCID 69342593, compoundYield 96.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent2×

Procedure

To a solution of 3.27 g of 5-fluoro-2-iodo-4-trifluoromethyl-aniline (10.7 mmol) in 20 ml triethylamine were added 3763 mg of Pd(PPh3)2Cl2 (0.5 mmol), 102 mg of CuI (0.5 mmol) and 1.63 ml of ethinyltrimethylsilane (11.8 mmol). The reaction mixture was stirred over night at rt before most of the triethylamine was removed under reduced pressure. Then DCM was added and the resulting suspension was filtered. The filtrate was then concentrated and the residue purified by chromatography (silica gel; cyclohexane/EtOAc 9:1) to yield 2.83 g (96%) of 5-fluoro-4-trifluoromethyl-2-trimethylsilanylethynyl-phenylamine contaminated with triethylamine as a dark red liquid. 1H-NMR (CDCl3, 300 MHz): δ 0.26 (s, 9H), 4.68 (br s, 2H), 6.44 (d, J=12 Hz, 1H), 7.51 (d, J=8 Hz, 1H).

Workup

  1. customwas removed under reduced pressure
  2. additionThen DCM was added
  3. filtrationthe resulting suspension was filtered
  4. concentrationThe filtrate was then concentrated
  5. customthe residue purified by chromatography (silica gel; cyclohexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-22a419fac97246f586a61090ade8bf45
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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