Phenylacetylene → HCID 66701096, compound

HRID 2075526Notes

Reaction equation

HRID 2075526 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1Br)=[O:9])([CH3:6])[CH3:5].[C:22]1([C:28]#[CH:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)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>[CH3:1][O:2][C:3](=[O:21])[C:4]([NH:7][C:8]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:29]#[C:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:9])([CH3:6])[CH3:5]

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 58370136HCID 58370136, compound

Product 1

HCID 66701096HCID 66701096, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

40 mg 2-[(1-Bromo-naphthalene-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester and 2 mg Bis(triphenylphosphine)palladium(II) chloride were suspended in 2 ml of DMF and deoxygenated with Argon. 0.26 ml of TMEDA were added, the mixture was again bubbled with Argon, and then 14 mg (0.137 mmol) phenylacetylene were added. After 14h at 80° the reaction was filtered, purified by RP-HPLC and freeze-dried to give 8 mg of 2-{[1-(Phenylethynyl)-naphthalene-2-carbonyl]-amino}-2-methyl-propionic acid methyl ester (19%).

Workup

  1. customdeoxygenated with Argon
  2. addition0.26 ml of TMEDA were added
  3. customthe mixture was again bubbled with Argon
  4. filtrationAfter 14h at 80° the reaction was filtered
  5. custompurified by RP-HPLC
  6. customfreeze-dried

Sources & evidence

ORD record
ord-c022d80e80d946b48d794a261237c667
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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