3-Fluoro-4-methylbenzenepropanal → HCID 66733772, compound

HRID 1929649Notes

Reaction equation

HRID 1929649 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]([CH2:20][CH2:21][CH:22]=O)[CH:16]=[CH:17][C:18]=1[CH3:19]>>[CH2:1]([C:3]1[N:4]2[CH2:9][CH2:10][NH:11][CH:22]([CH2:21][CH2:20][C:15]3[CH:16]=[CH:17][C:18]([CH3:19])=[C:13]([F:12])[CH:14]=3)[C:5]2=[C:6]([I:8])[N:7]=1)[CH3:2]

Participants

3

Reactant 2

HCID 534343213-Fluoro-4-methylbenzenepropanalHCID 66734063HCID 66734063, compound

Product 1

HCID 66733772HCID 66733772, compound

Procedure

According to the general procedure (GP10), the microwave-assisted Pictet-Spengler reaction (60 W; 100° C.; 8 bars; 10 min.) between 2-(2-ethyl-4-iodo-imidazol-1-yl)-ethylamine (320.7 mg; 1.210 mmol) and 3-(3-fluoro-4-methyl-phenyl)-propionaldehyde (202 mg; 1.210 mmol) afforded 3-ethyl-8-[2-(3-fluoro-4-methyl-phenyl)-ethyl]-1-iodo-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine which was Boc-protected and finally purified by HPLC.

Sources & evidence

ORD record
ord-6b1e9d98897f4e9084214ebf6b25f755
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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