2,4-Difluoro-3-methylbenzenepropanal → HCID 66733766, compound

HRID 1929652Notes

Reaction equation

HRID 1929652 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[C:18]([CH3:19])=[C:17]([F:20])[CH:16]=[CH:15][C:14]=1[CH2:21][CH2:22][CH:23]=O>>[F:12][C:13]1[C:18]([CH3:19])=[C:17]([F:20])[CH:16]=[CH:15][C:14]=1[CH2:21][CH2:22][CH:23]1[NH:11][CH2:10][CH2:9][N:4]2[C:3]([CH2:1][CH3:2])=[N:7][C:6]([I:8])=[C:5]12

Participants

3

Reactant 2

HCID 576596042,4-Difluoro-3-methylbenzenepropanalHCID 66734063HCID 66734063, compound

Product 1

HCID 66733766HCID 66733766, 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 (334.0 mg; 1.260 mmol) and 3-(2,4-difluoro-3-methyl-phenyl)-propionaldehyde (232.7 mg; 1.260 mmol) afforded 8-[2-(2,4-difluoro-3-methyl-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-c4c978173b144b5ab4a69b1a52512462
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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