2-Chloroacetophenone → 3-Thiocyano-2-methyl-7-phenacylpyrrolo[2,3-b]pyridine hydrochloride

HRID 1756081Notes

Reaction equation

HRID 1756081 reaction equation
[S:1]([C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[CH3:13])[C:2]#[N:3].[CH2:14]([Cl:23])[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16]>C(#N)C.CN(C)C=O>[ClH:23].[S:1]([C:4]1[C:12]2[C:7]([N:8]([CH2:14][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])[CH:9]=[CH:10][CH:11]=2)=[N:6][C:5]=1[CH3:13])[C:2]#[N:3]

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 193925873-Thiocyano-2-methylpyrrolo[2,3-b]pyridine

Product 1

HCID 199168253-Thiocyano-2-methyl-7-phenacylpyrrolo[2,3-b]pyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

A solution of 100 mg (0.53 mmol) of 3-thiocyano-2-methyl pyrrolo [2,3-b]pyridine and 122 mg (0.79 mmol) of phenacyl chloride in 3 ml acetonitrile: dimethylformamide 2:1 was warmed at 70° C. for 36 h. The reaction mixture was cooled to room temperature and the acetonitrile was evaporated. To the residue was added 10 ml diethyl ether. The precipitated product was filtered off and washed with acetonitrile giving 37 mg (23%) of the title compound.

Workup

  1. customthe acetonitrile was evaporated
  2. additionTo the residue was added 10 ml diethyl ether
  3. filtrationThe precipitated product was filtered off
  4. washwashed with acetonitrile giving 37 mg (23%) of the title compound

Sources & evidence

ORD record
ord-39e2a129642f417cb52c297092288909
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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