HCID 86657320, compound → HCID 58418018, compound

HRID 1908857Notes

Reaction equation

HRID 1908857 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=3)[N:9]=2)[CH:5]=[C:4]([CH3:20])[N:3]=1>O1CCOCC1.O>[CH2:5]([C:2]1[CH:7]=[C:6]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=3)[N:9]=2)[CH:5]=[C:4]([CH3:20])[N:3]=1)[CH:6]([CH3:8])[CH3:7]

Participants

4

Reactant 1

HCID 86657320HCID 86657320, compound

Product 1

HCID 58418018HCID 58418018, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-4-[3-(2-methyl-4-pyridinyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyridine (200 mg, 0.698 mmol) in dioxane (10 mL), Pd(dppf) (11 mg, 14 μmol) and isobutyl zink bromide (2.8 mL, 0.5 M in THF) is added. The mixture is stirred at 80° C. for 3 h before another portion of isobutyl zink bromide (2.8 mL) is added. Stirring is continued at 80° C. for 72 h. The mixture is cooled to rt, diluted with water and extracted with EA. The org. extract is concentrated and the crude product is purified by prep. HPLC to give 2-isobutyl-4-[3-(2-methyl-4-pyridinyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyridine (22 mg) as a beige solid; LC-MS: tR=0.71 min, [M+1]+=309.12.

Workup

  1. additionis added
  2. stirringStirring
  3. waitis continued at 80° C. for 72 h
  4. temperatureThe mixture is cooled to rt
  5. extractionextracted with EA
  6. extractionextract
  7. concentrationis concentrated
  8. customthe crude product is purified by prep

Sources & evidence

ORD record
ord-57ca0d40e0004f308ca32a7deff34de0
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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