Trimethylsilylacetylene → HCID 86725288, compound

HRID 1403201Notes

Reaction equation

HRID 1403201 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[O:9][CH3:10].[C:11]([Si:13]([CH3:16])([CH3:15])[CH3:14])#[CH:12]>C(#N)C.[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>[CH3:10][O:9][C:3]1[CH:4]=[C:5]([NH2:8])[CH:6]=[CH:7][C:2]=1[C:12]#[C:11][Si:13]([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 226370284-Iodo-3-methoxyaniline

Product 1

HCID 86725288HCID 86725288, compoundYield 66.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

4-Iodo-3-methoxy-phenylamine (3.17 g, 12.7 mmol) and ethynyl-trimethyl-silane (3.5 mL, 25 mmol) in dry acetonitrile were purged with nitrogen and treated with TEA (17.6 mL, 127 mmol), CuI (123 mg, 0.635 mmol) and Pd(Ph3P)2Cl2 (447 mg, 0.635 mmol). The reaction was stirred at room temperature for 2 h. The volatiles were evaporated, the residue was taken up with EtOAc (200 mL), washed with water (50 mL), dried over sodium sulfate and purified by flash chromatography on silica gel (hexane/EtOAc 55/45) to afford the title compound (1.86 g, 66%).

Workup

  1. customThe volatiles were evaporated
  2. washwashed with water (50 mL)
  3. dry with materialdried over sodium sulfate
  4. custompurified by flash chromatography on silica gel (hexane/EtOAc 55/45)

Sources & evidence

ORD record
ord-753b1e70251c472db9d920122895e3b8
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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