3-[4-(Trifluoromethoxy)phenyl]propanal → 3-Ethyl-1-iodo-8-[2-(4-trifluoromethoxy-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine

HRID 1929664Notes

Reaction equation

HRID 1929664 reaction equation
[CH2:1]([C:3]1[N:4]([CH2:9][CH2:10][NH2:11])[CH:5]=[C:6]([I:8])[N:7]=1)[CH3:2].[F:12][C:13]([F:26])([F:25])[O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH:23]=O)=[CH:17][CH:16]=1>>[CH2:1]([C:3]1[N:4]2[CH2:9][CH2:10][NH:11][CH:23]([CH2:22][CH2:21][C:18]3[CH:17]=[CH:16][C:15]([O:14][C:13]([F:12])([F:25])[F:26])=[CH:20][CH:19]=3)[C:5]2=[C:6]([I:8])[N:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 578340123-[4-(Trifluoromethoxy)phenyl]propanalHCID 66734063HCID 66734063, compound

Product 1

HCID 667339713-Ethyl-1-iodo-8-[2-(4-trifluoromethoxy-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine

Procedure

According to the general procedure (GP10), microwave-assisted Pictet-Spengler reaction (60 W; 140° C.; 6.5 bars; 10 min.) between 2-(2-ethyl-4-iodo-imidazol-1-yl)-ethylamine (5.621 mmol) and 3-(4-trifluoromethoxy-phenyl)-propionaldehyde (1.206 g; 5.528 mmol) afforded 3-ethyl-1-iodo-8-[2-(4-trifluoromethoxy-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine. LC-MS: tR=0.78 min.; [M+H]+=465.87 g/mol.

Sources & evidence

ORD record
ord-1ffbe887c5d241df954f43fe20211ede
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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