N,N'-Dimethylethylenediamine → HCID 58438637, compound

HRID 1898652Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[C:10]([CH:11]=[O:12])=[CH:9][N:8]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:5]2=[N:6][CH:7]=1.[Cl:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1[CH2:24][NH:25][C:26]2=[O:31].CNCCNC.C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.[Cu]I>[Cl:21][C:22]1[CH:30]=[CH:29][CH:28]=[C:27]2[C:23]=1[CH2:24][N:25]([C:2]1[N:3]=[C:4]3[C:10]([CH:11]=[O:12])=[CH:9][N:8]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:5]3=[N:6][CH:7]=1)[C:26]2=[O:31]

Participants

Conditions

Temperature: 100 °C

Procedure

A 10 mL flask was charged with 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (700 mg, 1.96 mmol), 4-chloro-2,3-dihydro-isoindol-1-one (395 mg, 2.36 mmol), N,N′-dimethylethylenediamine (42 μL, 0.39 mmol) and potassium carbonate (543 mg, 3.93 mmol) under argon atmosphere. Copper(I) iodide (37 mg, 0.20 mmol) was added and the reaction mixture was heated at 100° C. for 24 h. The reaction mixture was allowed to reach room temperature and then diluted with EtOAc (50 mL). The slurry was filtered over a celite pad and the filtrate was evaporated under vacuum. The crude residue was purified by column chromatography (SiO2, 100 g, EtOAc:hexanes, 0-70% in 30 min) to provide 170 mg (20%) of 2-(4-chloro-1-oxo-1,3-dihydro-isoindol-2-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde as an off-white solid and 400 mg of recovered starting material.

Workup

customto reach room temperature
filtrationThe slurry was filtered over a celite pad
customthe filtrate was evaporated under vacuum
customThe crude residue was purified by column chromatography (SiO2, 100 g, EtOAc:hexanes, 0-70% in 30 min)

Sources & evidence

ORD record: ord-42af37003a3d4a2ca5337e535d29d33d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518945B2

Reaction notes

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