N,N'-Dimethylethylenediamine → 2-[7-(2,2-Dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-2,3-dihydro-isoindol-1-one

HRID 547470Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1.[C:25]1(=[O:34])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][NH:26]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>C(OCC)(=O)C.[Cu](I)I.C1(C)C=CC=CC=1>[CH3:13][C:12]([CH3:15])([CH3:14])[C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([N:26]3[CH2:27][C:28]4[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:25]3=[O:34])[N:3]=2)[N:8]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:9]=1)=[O:16]

Participants

Conditions

Temperature: 110 °C

Procedure

Toluene was added to a mixture of 1-[2-Bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (0.250 g, 0.606 mmol), 2,3-Dihydro-isoindol-1-one (0.097 g, 0.727 mmol), copper iodide (11.6 mg, 0.061 mmol), and potassium carbonate (0.168 g, 1.212 mmol) under argon. Dimethyl ethylenediamine (0.013 mL; 0.011 g, 0.121 mmol) was subsequently added and the reaction was stirred for 16 h at 110° C. The reaction was diluted with ethyl acetate and filtered through a silica plug before being concentrated in vacuo. Silica gel chromatography (0->25% EtOAc/hexanes over 30 minutes) afforded 0.2206 g (78% yield) of 2-[7-(2,2-Dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-2,3-dihydro-isoindol-1-one. MS (E/I): 465 (M+H)

Workup

filtrationfiltered through a silica plug
concentrationbefore being concentrated in vacuo

Sources & evidence

ORD record: ord-9f2f46a2003b4870b1047460bab901b0
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939531B2

Reaction notes

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