HCID 57312439, compound → HCID 57309100, compound

HRID 1418379Notes

Reaction equation

HRID 1418379 reaction equation
[Cu][C:2]#[N:3].[CH2:4]1[O:22][C:7]2([CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:16]=[N:17][C:18](Br)=[CH:19][CH:20]=3)=[O:14])[CH2:9][CH2:8]2)[O:6][CH2:5]1>CN(C=O)C.O>[CH2:4]1[O:22][C:7]2([CH2:8][CH2:9][N:10]([C:13]([C:15]3[CH:16]=[N:17][C:18]([C:2]#[N:3])=[CH:19][CH:20]=3)=[O:14])[CH2:11][CH2:12]2)[O:6][CH2:5]1

Participants

5

Reactant 2

HCID 57312439HCID 57312439, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 57309100HCID 57309100, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A stirred suspension of copper (I) cyanide (0.66 g, 7.4 mmol) and 1-(6-bromo-3-pyridyl)carbonyl-4-piperidone ethylene ketal (2.2 g, 6.7 mmol, prepared as in Example V from 6-bromo-3-pyridinecarboxylic acid) in DMF (30 ml) was heated at 150° C. for 3 h. The mixture was cooled, diluted with water, extracted with ethyl acetate, dried over sodium sulphate and evaporated. Purification by flash chromatography on silica, eluting with 20% ethyl acetate/hexane, gave a white crystalline solid (0.96 g, 52%), m.p. 133°-135° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customPurification by flash chromatography on silica
  6. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3440aa5bdbe04577bdbcf2b02b017d0b
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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