Triethylamine → HCID 86648075, compound

HRID 1920122Notes

Reaction equation

HRID 1920122 reaction equation
[N:1]1[N:2]([C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19](Br)[C:20](=[O:24])[O:21]3)=[CH:16][CH:15]=2)[N:3]=[C:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=12.[CH3:26][Si:27]([C:30]#[CH:31])([CH3:29])[CH3:28].C(N(CC)CC)C>C1COCC1.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)I>[N:1]1[N:2]([C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([C:31]#[C:30][Si:27]([CH3:29])([CH3:28])[CH3:26])[C:20](=[O:24])[O:21]3)=[CH:16][CH:15]=2)[N:3]=[C:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=12

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 86648076HCID 86648076, compound

Product 1

HCID 86648075HCID 86648075, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

After charging 7.8 parts of 7-(naphtho[1,2]triazol-2-yl)-3-bromocoumarin synthesized by a known method, 2.4 parts of trimethylsilylacetylene, 0.46 parts of tetrakis(triphenylphosphine)palladium(0), 0.038 parts of copper iodide and 20 ml of triethylamine in 40 ml of THF, the mixture was refluxed for 9 hours. The reaction mixture was filtered and washed with THF, and the obtained filtrate was concentrated and then diluted with water and filtered. The obtained cake was recrystallized from methanol. Upon drying under reduced pressure there was obtained 4 parts of 7-(naphtho[1,2]triazol-2-yl)-3-trimethylsilylethynylcoumarin having a melting point of 250-252° C.

Workup

  1. temperaturethe mixture was refluxed for 9 hours
  2. filtrationThe reaction mixture was filtered
  3. washwashed with THF
  4. concentrationthe obtained filtrate was concentrated
  5. additiondiluted with water
  6. filtrationfiltered
  7. customThe obtained cake was recrystallized from methanol
  8. customUpon drying under reduced pressure

Sources & evidence

ORD record
ord-1cf2138326a34d28ba0fad3374cebdd3
Source dataset
uspto-grants-2012_05
Patent number
US08168796B2

Reaction notes

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