Phenethyl bromide → 2,3-Dimethyl-6-methylthio-7-phenethylpyrrolo[2,3-b]pyridine

HRID 1756070Notes

Reaction equation

HRID 1756070 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](Br)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC#N>[CH3:1][C:2]1[N:12]=[C:5]2[N:6]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]([S:10][CH3:11])=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:13]

Participants

4

Reactant 2

HCID 7666Phenethyl bromideHCID 193926102,3-Dimethyl-6-mehylthiopyrrolo[2,3-b]pyridine

Product 1

HCID 193925812,3-Dimethyl-6-methylthio-7-phenethylpyrrolo[2,3-b]pyridineYield 13.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A refluxing solution of 2,3-dimethyl-6-mehylthiopyrrolo[2,3-b]pyridine (100 mg, 0.5 mmol) in 5 ml CH3CN was treated with five portions of phenethyl bromide (85 μl, 1.2 mmol), one each 24 h. The solvent was evporated and the residue chromatographed (silica, CH2Cl2 saturated with NH3 /diethyl ether/petroleum ether; 5/2/3) affording 20 mg (13%) pure title compound.

Workup

  1. customthe residue chromatographed (silica, CH2Cl2 saturated with NH3 /diethyl ether/petroleum ether; 5/2/3)

Sources & evidence

ORD record
ord-846f110eaa5b4ec9ba36573368649fbd
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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