Butyryl chloride → HCID 21914106, compound

HRID 1246212Notes

Reaction equation

HRID 1246212 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:13](=[N:15][OH:16])[NH2:14])(=[O:3])[CH3:2].[C:17](Cl)(=O)[CH2:18][CH2:19][CH3:20]>N1C=CC=CC=1>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:13]1[N:14]=[C:17]([CH2:18][CH2:19][CH3:20])[O:16][N:15]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 73853099HCID 73853099, compound

Product 1

HCID 21914106HCID 21914106, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of intermediate (14) (0.00898 mole) and butanoyl chloride (0.0094 mole) in pyridine (140 ml) was stirred at room temperature for 40 hours and then heated to reflux. After 21 hours the reaction was cooled and concentrated in vacuo. The residue was extracted between DCM and saturated aqueous NaHCO3 and the organic fraction was dried over Na2SO4, filtered, and concentrated.The residue was subjected to silica gel flash column chromatography (eluent 100% CH2Cl2 to 95/5 CH2Cl2/ether), yielding 1-acetyl-2,3-dihydro-2-(5-propyl-1,2,4-oxadiazol-3-yl)-1H-indole (compound 89, mp. 93–94° C.).

Workup

  1. temperatureheated to reflux
  2. temperatureAfter 21 hours the reaction was cooled
  3. concentrationconcentrated in vacuo
  4. extractionThe residue was extracted between DCM and saturated aqueous NaHCO3
  5. dry with materialthe organic fraction was dried over Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-fb7e91b95c5b41439b2c55c140507861
Source dataset
uspto-grants-2006_10
Patent number
US07125891B2

Reaction notes

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