Propargyl alcohol → 3-(3-(Pyridin-2-yl)isoxazol-5-yl)prop-2-yn-1-ol

HRID 2416540Notes

Reaction equation

HRID 2416540 reaction equation
I[C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:3]=1.[CH2:13]([OH:16])[C:14]#[CH:15]>C(N(CC)CC)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>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[CH:3]=[C:2]([C:15]#[C:14][CH2:13][OH:16])[O:6][N:5]=1

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 111499432-(5-Iodo-3-isoxazolyl)pyridine

Product 1

HCID 226308213-(3-(Pyridin-2-yl)isoxazol-5-yl)prop-2-yn-1-olYield 22%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 2-(5-iodo-3-isoxazolyl)pyridine (prepared as described in WO0232919, 1.38 g, 5 mmol) and dichlorobis(triphenylphosphine)palladium(II) (35 mg, 0.05 mmol) in 8 mL triethylamine was degassed with nitrogen. Propargyl alcohol (560 mg, 10 mmol) was added and the mixture was heated at 65° C. for 16 h. The reaction mixture was cooled to room temperature, concentrated to remove the solvent. The residue was diluted with ethyl acetate (100 mL), washed with saturated NaHCO3, water and brine. The organic layer was dried and concentrated. Purification by chromatography (SiO2, 1:1 hexane/ethyl acetate) yielded 220 mg (22%) of the title compound. MS 201 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customto remove the solvent
  4. additionThe residue was diluted with ethyl acetate (100 mL)
  5. washwashed with saturated NaHCO3, water and brine
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customPurification by chromatography (SiO2, 1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-91ad6aa925084cb794ab447d20a021fb
Source dataset
uspto-grants-2004_11
Patent number
US06825170B2

Reaction notes

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