Triethylamine → HCID 69364816, compound

HRID 397312Notes

Reaction equation

HRID 397312 reaction equation
[CH3:1][O:2][C:3](=[O:17])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([O:14][CH3:15])=[O:13])=[C:7](I)[CH:6]=1.C(N(CC)CC)C.[Cl:25][CH2:26][CH2:27][CH2:28][C:29]#[CH:30]>C(#N)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:1][O:2][C:3](=[O:17])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([O:14][CH3:15])=[O:13])=[C:7]([C:30]#[C:29][CH2:28][CH2:27][CH2:26][Cl:25])[CH:6]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 843081-Pentyne, 5-chloro-HCID 69363848HCID 69363848, compound

Product 1

HCID 69364816HCID 69364816, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Carbonic acid 3-iodo-4-methoxycarbonylamino-phenyl ester methyl ester (28.0 g, 79.75 mmol) was dissolved in acetonitrile (350 mL). Triethylamine (22.2mL, 160 mmol), Copper (I) iodide (300 mg, 1.58 mmol), bis(triphenylphosphine)palladium (II) chloride (1.12 g, 1.6 mmol) and 5-chloro-1-pentyne (10.0 mL, 95.54 mmol) were added and the mixture heated 3 h at 70° C. The reaction was cooled and partitioned between ethyl acetate (100 mL) and IM pH4 phosphate buffer (100 mL). The phases were separated, the aqueous phase extracted with ethyl acetate and the combined organic phases washed with 10% sodium thiosulfate solution, brine, dried over sodium sulfate and evaporated. The orange/brown residue (23.5 g, 90%) was used without further purification. (A small sample was purified by column chromatography on silica gel (5:1 hexane/ethyl acetate) for analytical purposes). ISP-MS: m/e=326.3 ([M−H]+)

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between ethyl acetate (100 mL) and IM pH4 phosphate buffer (100 mL)
  3. customThe phases were separated
  4. extractionthe aqueous phase extracted with ethyl acetate
  5. washthe combined organic phases washed with 10% sodium thiosulfate solution, brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe orange/brown residue (23.5 g, 90%) was used without further purification
  9. custom(A small sample was purified by column chromatography on silica gel (5:1 hexane/ethyl acetate) for analytical purposes)

Sources & evidence

ORD record
ord-b07e480cc427443bb53ffb1399ce6312
Source dataset
uspto-grants-2003_08
Patent number
US06610685B2

Reaction notes

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