4-Pentynoic acid → HCID 178525391, compound

HRID 2289976Notes

Reaction equation

HRID 2289976 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18](I)=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1.[C:25]([OH:31])(=[O:30])[CH2:26][CH2:27][C:28]#[CH:29]>C(NCC)C.[Cu](I)I.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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([C:29]#[C:28][CH2:27][CH2:26][C:25]([OH:31])=[O:30])=[CH:17][C:16]=3[F:24])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 224644-Pentynoic acidHCID 178522917HCID 178522917, compound

Product 1

HCID 178525391HCID 178525391, compoundYield 13.4%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8021DiethylamineSolvent

Procedure

To a mixture of the title compound of Example 5 (0.457 g), copper iodide (0.010 g) and dichlorobis(triphenylphosphine)palladium (II) (0.035 g) in 15 mL diethylamine is added 4-pentynoic acid (0.098 g). The reaction is allowed to stir overnight. The solvents are evaporated and the residue is chromatographed on silica, eluting with 10% MeOH/CH2Cl2. Fractions homogeneous by TLC are combined and condensed. The residue is recrysallized from acetone/hexanes to yield 0.057 g of the desired product as a tan solid.

Workup

  1. customThe solvents are evaporated
  2. customthe residue is chromatographed on silica
  3. washeluting with 10% MeOH/CH2Cl2
  4. customcondensed

Sources & evidence

ORD record
ord-8ea4722daf224acdbc285b7a3631cd2f
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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