Sodium Carbonate → 5-Cyano-2,3-dimethyl-7-phenacyl pyrrolo[2,3-b]pyridine

HRID 1756076Notes

Reaction equation

HRID 1756076 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:11]([CH3:12])=[C:10]([CH3:13])[NH:9][C:6]2=[N:7][CH:8]=1)#[N:2].[CH2:14](Cl)[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16].C([O-])([O-])=O.[Na+].[Na+]>CC#N>[C:1]([C:3]1[CH:4]=[C:5]2[C:11]([CH3:12])=[C:10]([CH3:13])[N:9]=[C:6]2[N:7]([CH2:14][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])[CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 107572-ChloroacetophenoneHCID 193925855-Cyano-2,3-dimethyl-pyrrolo[2,3-b]pyridine

Product 1

HCID 199167675-Cyano-2,3-dimethyl-7-phenacyl pyrrolo[2,3-b]pyridineYield 26%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-cyano-2,3-dimethyl-pyrrolo [2,3-b]pyridine (77 mg, 0.5 mmol ) and phenacyl chloride (650 mg, 4.2 mmol ) in 12 ml CH3CN was refluxed for 62 h. The mixture was basified with a saturated Na2CO3 solution and extracted with CH2Cl2. The organic layer was dried over MgSO4 and evaporated. The residue was chromatographed (silica, CH2Cl2 /diethyl ether;7/3) yielding 34 mg (26%) pure title compound.

Workup

  1. temperaturewas refluxed for 62 h
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated
  5. customThe residue was chromatographed (silica, CH2Cl2 /diethyl ether;7/3)

Sources & evidence

ORD record
ord-87ee807f070148eb94dc2148a6ccabbc
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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