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Triethylamine → HCID 87422751, compound

HRID 1920121
Notes
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Reaction equation

HRID 1920121 reaction equation
[CH2:1]([N:3]([CH2:22][CH3:23])[C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:15]3[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=3)=[CH:9][C:10](=[O:14])[O:11]2)=[CH:6][CH:5]=1)[CH3:2].[C:24]1([C:30]#[CH:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.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>[CH2:1]([N:3]([CH2:22][CH3:23])[C:4]1[CH:13]=[C:12]2[C:7]([C:8]([C:15]3[CH:20]=[CH:19][C:18]([C:31]#[C:30][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:17][CH:16]=3)=[CH:9][C:10](=[O:14])[O:11]2)=[CH:6][CH:5]=1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 87422732HCID 87422732, compound

Product 1

HCID 87422751HCID 87422751, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalyst
HCID 178418397
HCID 178418397, compound
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

After charging 7.4 parts of 7-diethylamino-4-[(p-bromphenyl)]coumarin synthesized by a known method, 2.4 parts of phenylacetylene, 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 2.2 parts of 7-diethylamino-4-[4-(phenylethynyl)phenyl]coumarin having a melting point of 136-138° 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-3cc4216e2e4d406db9bd93f1a732cd24
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08168796B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes