Water → HCID 25181652, compound

HRID 1896016Notes

Reaction equation

HRID 1896016 reaction equation
[N+:1]([C:4]1[C:5]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=O)[CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:19]1([C:25]#[CH:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1.S(Cl)(Cl)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:1]([C:4]1[C:5]([N:10]2[CH2:11][CH2:12][CH:13]([C:16](=[O:18])[C:26]#[C:25][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][CH2:15]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 16788087HCID 16788087, compound

Product 1

HCID 25181652HCID 25181652, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

To a solution of Compound 258b in anhydrous toluene (10 mL), thionyl chloride (0.29 mL, 3.98 mmol was added and the resulting mixture was stirred at reflux for 1 hour, cooled to r.t and evaporated to dryness in vacuo. The residue was dissolved in anhydrous toluene (5 mL); to this solution was added phenylacetylene (0.09 mL, 0.80 mmol), palladium(II)acetate (18 mg, 0.08 mmol), triethylamine (0.34 mL, 2.4 mmol). The mixture was stirred in a microwave oven at 110° C. for 1 hour, cooled to r.t., poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether 25:75) affording the title product (77 mg).

Workup

  1. temperatureat reflux for 1 hour
  2. temperaturecooled
  3. customevaporated to dryness in vacuo
  4. dissolutionThe residue was dissolved in anhydrous toluene (5 mL)
  5. stirringThe mixture was stirred in a microwave oven at 110° C. for 1 hour
  6. extractionextracted with EtOAc
  7. washThe combined organic layers were washed with brine
  8. customdried on Na2SO4
  9. customevaporated to dryness in vacuo
  10. customto afford a residue, which
  11. customwas purified by flash chromatography (EtOAc—Petroleum Ether 25:75)

Sources & evidence

ORD record
ord-e525a676c1244105a648589fdfa4d986
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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