Hydrochloric Acid → HCID 18706394, compound

HRID 1422259Notes

Reaction equation

HRID 1422259 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[N:9]2)=[C:4](I)[CH:3]=1.[CH2:17]([OH:20])[C:18]#[CH:19].C(N(CC)CC)C.Cl>CN(C)C=O.[Cl-].[Na+].O.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.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[N:9]2)=[C:4]([C:19]#[C:18][CH2:17][OH:20])[CH:3]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 18706701HCID 18706701, compound

Product 1

HCID 18706394HCID 18706394, compoundYield 10.7%

Reagents, catalysts & solvents 5

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
70 °C

Procedure

12.9 g (36.8 mmol) of 7-chloro-2,3-dimethoxy-5-iodo-quinoxaline, 7.6 ml (128.4 mmol) of propargyl alcohol, 2.1 g (3 mmol) of bis(triphenylphosphine)-palladium dichloride, 6.6 ml (47.4 mmol) of triethylamine and 0.34 g (1.8 mmol) of cuprous iodide are placed in 125 ml of dimethylformamide and heated to a bath temperature of 70° C. The reaction mixture is then stirred for 3.5 hours at that temperature and then cooled to room temperature. Ethyl acetate is added to the reaction mixture and extraction is carried out with water, 1N hydrochloric acid and brine. The aqueous phases are washed with ethyl acetate. The organic phases are combined, dried over sodium sulfate, filtered with suction and concentrated. Chromatography of the crude product on silica gel with hexane/ethyl acetate (3:1) yields 1.1 g of 3-(7-chloro-2,3-dimethoxy-quinoxalin-5-yl)-prop-2-yn-1-ol in the form of brown crystals having a melting point of 137-140° C.

Workup

  1. temperaturecooled to room temperature
  2. washThe aqueous phases are washed with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered with suction
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-00622cf26dbb45478c3038fdde33a6f3
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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