3-[4-(Trifluoromethyl)phenyl]propanal → HCID 66734104, compound

HRID 1929657Notes

Reaction equation

HRID 1929657 reaction equation
[I:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH2:8][NH2:9])[CH:6]=1.[F:10][C:11]([F:23])([F:22])[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH:20]=O)=[CH:14][CH:13]=1>>[I:1][C:2]1[N:3]=[CH:4][N:5]2[CH2:7][CH2:8][NH:9][CH:20]([CH2:19][CH2:18][C:15]3[CH:16]=[CH:17][C:12]([C:11]([F:10])([F:22])[F:23])=[CH:13][CH:14]=3)[C:6]=12

Participants

3

Reactant 2

HCID 216838073-[4-(Trifluoromethyl)phenyl]propanalHCID 58247266HCID 58247266, compound

Product 1

HCID 66734104HCID 66734104, compound

Procedure

According to the general procedure (GP10), the microwave-assisted Pictet-Spengler reaction (70 W; 130° C.; 10 bars; 10 min.) between 2-(4-iodo-imidazol-1-yl)-ethylamine (4.326 g; 18.253 mmol) and 3-(4-trifluoromethyl-phenyl)-propionaldehyde (3.690 g; 18.253 mmol) afforded 1-iodo-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-7cd3beb6c59b4b7f88efc329505e25f6
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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