2-Chloroacetophenone → 2,3-Dimethyl-6-methylthio-7-phenacylpyrrolo[2,3-b]pyridine

HRID 1756071Notes

Reaction equation

HRID 1756071 reaction equation
[CH3:1][C:2]1[NH:12][C:5]2=[N:6][C:7]([S:10][CH3:11])=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:13].[CH2:14](Cl)[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16]>CC#N>[CH3:1][C:2]1[N:12]=[C:5]2[N:6]([CH2:14][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])[C:7]([S:10][CH3:11])=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:13]

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 193926102,3-Dimethyl-6-mehylthiopyrrolo[2,3-b]pyridine

Product 1

HCID 199168092,3-Dimethyl-6-methylthio-7-phenacylpyrrolo[2,3-b]pyridineYield 41.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,3-dimethyl-6-methylthiopyrrolo[2,3-b]pyridine (100 mg, 0.5 mmol) and phenacyl chloride (804 mg, 5 mmol) in 3 ml CH3CN was refluxed for 72 h. The solvent was evaporated and the residue chromatographed (silica, CH2Cl2 /MeOH;59/5). Pure fractions were pooled, evaporated, and taken up in 100 ml CH2Cl2. The organic layer was washed with 25 ml 2M HCl, dried over MgSO4, and evaporated leaving 64 mg (35%) pure product as the hydrochloride.

Workup

  1. temperaturewas refluxed for 72 h
  2. customThe solvent was evaporated
  3. customthe residue chromatographed (silica, CH2Cl2 /MeOH;59/5)
  4. customevaporated
  5. washThe organic layer was washed with 25 ml 2M HCl
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-306b8c7de9b54e9a9f9a3526c70b58b8
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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