Pyridine → HCID 18509387, compound

HRID 1356813Notes

Reaction equation

HRID 1356813 reaction equation
[CH3:1][C:2]([CH3:22])([CH3:21])[C:3]#[C:4][CH:5]=[CH:6][CH2:7][N:8]([CH2:10][C:11]1[CH:12]=[C:13](C(O)(C)C)[CH:14]=[CH:15][CH:16]=1)[CH3:9].S(Cl)(Cl)=O.N1C=C[CH:30]=[CH:29][CH:28]=1>>[CH3:22][C:2]([CH3:1])([CH3:21])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:29]([CH3:30])=[CH2:28])[CH3:9]

Participants

4

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 86759057HCID 86759057, compound

Product 1

HCID 18509387HCID 18509387, compoundYield 40.8%

Procedure

A mixture of pyridine (10 ml), Compound 37 (940 mg; 3.1 mmol), and thionyl chloride (1.12 g; 9.4 mmol) was stirred for 15 minutes while being cooled with ice, and then stirred for 15 minutes at room temperature. Subsequently, unreacted pyridine and thionyl chloride were evaporated under reduced pressure, and saturated aqueous sodium bicarbonate solution was added thereto. The mixture was extracted with ether twice (70 ml and 50 ml), and the combined organic layer was washed with saturated brine, followed by drying over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1), to thereby yield 360 mg of the target compound (yield: 40.8%).

Workup

  1. temperaturewhile being cooled with ice
  2. stirringstirred for 15 minutes at room temperature
  3. customSubsequently, unreacted pyridine and thionyl chloride were evaporated under reduced pressure, and saturated aqueous sodium bicarbonate solution
  4. additionwas added
  5. extractionThe mixture was extracted with ether twice (70 ml and 50 ml)
  6. washthe combined organic layer was washed with saturated brine
  7. dry with materialby drying over magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-219110a2e50343c5805988f1d287db95
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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