Trimethylsilylacetylene → [5-(Methylsulfonyl)-2-[2-(trimethylsilyl)ethynyl]phenyl][4-[4-(trifluoromethyl)phenyl]-1-piperazinyl]methanone

HRID 2374235Notes

Reaction equation

HRID 2374235 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:12]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)=[O:13].[C:30]([Si:32]([CH3:35])([CH3:34])[CH3:33])#[CH:31]>C(N(CC)CC)C.C(OC(=O)C)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([C:31]#[C:30][Si:32]([CH3:35])([CH3:34])[CH3:33])=[C:3]([C:12]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[CH:4]=1)(=[O:10])=[O:9]

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 59793691(2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone

Product 1

HCID 59853658[5-(Methylsulfonyl)-2-[2-(trimethylsilyl)ethynyl]phenyl][4-[4-(trifluoromethyl)phenyl]-1-piperazinyl]methanoneYield 53%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (2-Iodo-5-methanesulfonyl-phenyl)-[4-(4-trifluoromethyl-phenyl)-piperazin-1-yl]-methanone, Example 9 (100 mg, 0.186 mmol), Pd(PPh3)4 (10 mg, 0.0093 mmol), CuI (1.8 mg, 0.0093 mmol) and Ethynyltrimethylsilane (32 ul, 0.223 mmol) in triethylamine (0.4 ml) was heated to 80° C. for 4 hours. The mixture was cooled to room temperature, diluted with ethylacetate, filtered and the solvent was removed in vacuo. The crude brown oil was purified on SiO2 (Heptane/AcOEt 0%-40%,15 minutes) to provide the title compound (50 mg, 53%, yellow foam); M+H=590.2.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. customthe solvent was removed in vacuo
  4. customThe crude brown oil was purified on SiO2 (Heptane/AcOEt 0%-40%,15 minutes)

Sources & evidence

ORD record
ord-6d29d023f04b47b59993d08b37e490e8
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

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