Phenacyl bromide → HCID 19916777, compound

HRID 1756065Notes

Reaction equation

HRID 1756065 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]#[N:13])=[C:9]([CH3:14])[NH:8][C:5]2=[N:6][CH:7]=1.[CH2:15](Br)[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17]>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]([CH2:11][C:12]#[N:13])=[C:9]([CH3:14])[N:8]=[C:5]2[N:6]([CH2:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:17])[CH:7]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 19392579HCID 19392579, compound

Product 1

HCID 19916777HCID 19916777, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-chloro-3-cyanomethyl-2-methyl-pyrrolo[2,3-b]pyridine (147 mg, 0.7 mmol) and phenacylbromide (142 g, 7 mmol) in 12 ml CH3CN was refluxed for 22h. The reaction mixture was cooled and precipitated title compound was collected and washed with small portions of ice cold diethyl ether. Treatment of the filtrate with diethyl ether afforded a second and third lot of pure title compound. Total yield 257 mg (91%) calculated as the hydrobromide.

Workup

  1. temperaturewas refluxed for 22h
  2. temperatureThe reaction mixture was cooled
  3. customprecipitated title compound
  4. customwas collected
  5. washwashed with small portions of ice cold diethyl ether

Sources & evidence

ORD record
ord-03ef64b31f2a4aaba435c8b4a386220d
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

Loading…