Hydrochloric Acid → HCID 57543456, compound

HRID 2101259Notes

Reaction equation

HRID 2101259 reaction equation
[CH3:1][O:2][C:3](=[O:14])[NH:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([Cl:12])=[CH:7][C:6]=1I.[C:15]([Si:17]([CH3:20])([CH3:19])[CH3:18])#[CH:16].Cl>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>[CH3:1][O:2][C:3](=[O:14])[NH:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([Cl:12])=[CH:7][C:6]=1[C:16]#[C:15][Si:17]([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 66111TrimethylsilylacetyleneHCID 57438502HCID 57438502, compound

Product 1

HCID 57543456HCID 57543456, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
0 °C

Procedure

Pd(PPh3)2Cl2 (153 mg, 0.22 mmol) and copper(I)iodide (42 mg, 0.22 mmol) were dissolved in triethylamine (40 ml) and refluxed under argon for 20 min. The reaction mixture was then cooled down to 0° C. and (4-chloro-5-fluoro-2-iodo-phenyl)-carbamic acid methyl ester (7.2 g, 21 mmol) was added. After 10 min stirring at rt, ethinyltrimethylsilane (3.45 ml, 24.9 mmol) was added dropwise (exothermic, temperature raises from 18 to 33° C.) and the reaction mixture was stirred for one hour at rt. The reaction mixture was then poured on 1N aq. HCl solution (180 ml) and ice and extracted twice with ethyl acetate (180 ml). The combined organic phases were washed with water and sat. aq. NaCl solution, dried over magnesium sulfate, filtered and concentrated in vacuo to yield crude (4-chloro-5-fluoro-2-trimethylsilanylethynyl-phenyl)-carbamic acid methyl ester.

Workup

  1. temperaturerefluxed under argon for 20 min
  2. temperature(exothermic, temperature raises from 18 to 33° C.)
  3. stirringthe reaction mixture was stirred for one hour at rt
  4. extractionextracted twice with ethyl acetate (180 ml)
  5. washThe combined organic phases were washed with water and sat. aq. NaCl solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29ca9562a7094645bf5eaee06eb0c2f3
Source dataset
uspto-grants-2009_08
Patent number
US07572823B2

Reaction notes

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