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

HRID 1929669Notes

Reaction equation

HRID 1929669 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]1[CH:14]=[C:15]([CH2:21][CH2:22][CH:23]=O)[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]>>[CH2:1]([C:3]1[N:4]2[CH2:9][CH2:10][NH:11][CH:23]([CH2:22][CH2:21][C:15]3[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:13]([F:12])[CH:14]=3)[C:5]2=[C:6]([I:8])[N:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 626052953-(3-Fluoro-4-methoxyphenyl)propanalHCID 66734063HCID 66734063, compound

Product 1

HCID 667341123-Ethyl-8-[2-(3-fluoro-4-methoxy-phenyl)-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 (11.500 mmol) and 3-(3-fluoro-4-methoxy-phenyl)-propionaldehyde (2.514 g; 13.800 mmol) afforded 3-ethyl-8-[2-(3-fluoro-4-methoxy-phenyl)-ethyl]-1-iodo-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine. LC-MS: tR=0.70 min.; [M+H]+=429.88 g/mol.

Sources & evidence

ORD record
ord-ee4ce9f0e2b345ca8e369f5e4e1e8896
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

Loading…