Triethylamine → 2-(4-Methoxymethylthiophenyl]3-(4-pyridyl) 6,7-dihydro[5H]pyrrolo[1,2-a]imidazole

HRID 1885600Notes

Reaction equation

HRID 1885600 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH2:21][CH2:20][CH2:19][N:11]3[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:29][O:30][CH2:31]Br>C(Cl)Cl>[CH3:29][O:30][CH2:31][S:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH2:21][CH2:20][CH2:19][N:11]3[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83093Bromomethyl methyl etherHCID 135962046(4-mercaptophenyl) 3 (4-pyridyl) 6,7dihydro[5H]-pyrrolo[1,2-a]imidazole

Product 1

HCID 1317168132-(4-Methoxymethylthiophenyl]3-(4-pyridyl) 6,7-dihydro[5H]pyrrolo[1,2-a]imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-bath cooled solution containing 1.0 g (3.4 mmole) of 2-(4-mercaptophenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2 -a]imidazole prepared as in Example 16 and 0.5 ml (3.6 mmole) of triethylamine in 10 ml of methylene chloride is added 0.27 ml (3.5 mmole) of bromomethyl methyl ether. The reaction is allowed to warm to room temperature and stirred at room temperature for several hours. Workup and chromatography in a manner analogous to that outlined in example 18 affords the desired titled compound.

Workup

  1. temperatureTo an ice-bath cooled solution
  2. additioncontaining

Sources & evidence

ORD record
ord-6af76efa9d154b0fb1661c69411fbb72
Source dataset
uspto-grants-1992_09
Patent number
US05145858

Reaction notes

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