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

HRID 1929665Notes

Reaction equation

HRID 1929665 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].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]=O)=[CH:15][CH:14]=1>>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]2[NH:11][CH2:10][CH2:9][N:4]3[C:3]([CH2:1][CH3:2])=[N:7][C:6]([I:8])=[C:5]23)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 114812883-(4-Bromophenyl)propanalHCID 66734063HCID 66734063, compound

Product 1

HCID 667340678-[2-(4-Bromo-phenyl)-ethyl]-3-ethyl-1-iodo-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 (26.610 mmol) and 3-(4-bromo-phenyl)-propionaldehyde (6.350 g; 29.803 mmol) afforded 8-[2-(4-bromo-phenyl)-ethyl]-3-ethyl-1-iodo-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine. LC-MS: tR=0.74 min.; [M+H]+=460.01 g/mol.

Sources & evidence

ORD record
ord-80f8633edd8a420e8189334a9af1d6e8
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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