3-(3,4-Difluorophenyl)propanal → HCID 66733731, compound

HRID 1929646Notes

Reaction equation

HRID 1929646 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[F:19]>>[F:12][C:13]1[CH:14]=[C:15]([CH2:20][CH2:21][CH:22]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:16]=[CH:17][C:18]=1[F:19]

Participants

3

Reactant 2

HCID 534250903-(3,4-Difluorophenyl)propanalHCID 66734063HCID 66734063, compound

Product 1

HCID 66733731HCID 66733731, 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 (355.2 mg; 1.340 mmol) and 3-(3,4-difluoro-phenyl)-propionaldehyde (228.7 mg; 1.340 mmol) afforded 8-[2-(3,4-difluoro-phenyl)-ethyl]-3-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-3193de90f6c84adf94f436dfe3c3e76b
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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