Chloride → HCID 13849599, compound

HRID 580293Notes

Reaction equation

HRID 580293 reaction equation
[CH:1]#[C:2][CH3:3].I[C:5]1[C:10](=[O:11])[NH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([C:16]([O:18][CH3:19])=[O:17])[CH:6]=1.[Cl-].O>CS(C)=O.C(N(CC)CC)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(Cl)Cl>[CH3:1][C:2]1[O:11][C:10]2=[N:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([C:16]([O:18][CH3:19])=[O:17])[CH:6]=[C:5]2[CH:3]=1

Participants

10

Reactant 4

HCID 312ChlorideHCID 962WaterHCID 6335Propyne2×HCID 14838731HCID 14838731, compound

Product 1

HCID 13849599HCID 13849599, compound

Reagents, catalysts & solvents 5

HCID 178419050HCID 178419050, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Propyne (3.0 mLs, 0.045 mol) is condensed in a graduated cylinder in a dry ice/acetone bath and added to a stirred suspension of dimethyl 1,6-dihydro-5-iodo-6-oxo-2,3-pyridinedicarboxylate (13.48 g, 0.04 mol), cuprous iodide (0.38 g, 0.002 mol) and bis(triphenylphosphine)palladium II) chloride (2.81 g, 0.004 mol) in 150 mLs DMSO and 50 mLs triethylamine at 10° C. After addition of the propyne the reaction mixture is stirred at room temperature for 60 hours. Water is added and the mixture is extracted with ethyl acetate. The ethyl acetate solution is washed with water and dried over anhydrous MgSO4, then concentrated in vacuo to give a mixture of materials. The crude product is isolated by flash column chromatography using 9:1 methylene chloride:ethyl acetate. The fractions containing the title product are concentrated in vacuo and the residue is recrystallized from cyclohexane to give the pure compound mp 115°-118° C.

Workup

  1. customcondensed in a graduated cylinder in a dry ice/acetone bath
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe ethyl acetate solution is washed with water
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give
  7. additiona mixture of materials
  8. customThe crude product is isolated by flash column chromatography

Sources & evidence

ORD record
ord-1447b96e9d814b258557823411efd355
Source dataset
uspto-grants-1988_06
Patent number
US04752323

Reaction notes

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