3-[4-(Trifluoromethyl)phenyl]propanal → HCID 66733993, compound

HRID 1929653Notes

Reaction equation

HRID 1929653 reaction equation
[I:1][C:2]1[N:3]=[C:4]([CH3:10])[N:5]([CH2:7][CH2:8][NH2:9])[CH:6]=1.[F:11][C:12]([F:24])([F:23])[C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH:21]=O)=[CH:15][CH:14]=1>>[I:1][C:2]1[N:3]=[C:4]([CH3:10])[N:5]2[CH2:7][CH2:8][NH:9][CH:21]([CH2:20][CH2:19][C:16]3[CH:17]=[CH:18][C:13]([C:12]([F:11])([F:23])[F:24])=[CH:14][CH:15]=3)[C:6]=12

Participants

3

Reactant 2

HCID 216838073-[4-(Trifluoromethyl)phenyl]propanalHCID 667339802-(4-Iodo-2-methyl-imidazol-1-yl)-ethylamine

Product 1

HCID 66733993HCID 66733993, compound

Procedure

According to the general procedure (GP10), the microwave-assisted Pictet-Spengler reaction (60 W; 110° C.; 8 bars; 10 min.) between 2-(4-iodo-2-methyl-imidazol-1-yl)-ethylamine (373.8 mg; 1.489 mmol) and 3-(4-trifluoromethyl-phenyl)-propionaldehyde (301 mg; 1.489 mmol) afforded 1-iodo-3-methyl-8-[2-(4-trifluoromethyl-phenyl)-ethyl]-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine which was Boc-protected and finally purified by FC (DCM/MeOH=25/1).

Sources & evidence

ORD record
ord-176a9bceabc942468e6e5b31c87f3bda
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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