Trifluoroacetic acid → 2-(7-Iodo-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl)-isoindole-1,3-dione

HRID 1616879Notes

Reaction equation

[I:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]([CH2:9][CH2:10][NH2:11])=[CH:7][O:8][C:4]=2[CH:3]=1.O=[C:15]([CH3:28])[CH2:16][N:17]1[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]1=[O:27].FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[I:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6]3[CH2:9][CH2:10][NH:11][C:15]([CH2:16][N:17]4[C:25](=[O:26])[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[C:18]4=[O:27])([CH3:28])[C:7]=3[O:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2-(6-iodo-benzofuran-3-yl)-ethylamine (2.00 g, 6.97 mmol) and 2-(2-oxo-propyl)-isoindole-1,3-dione (4.25 g, 20.9 mmol) was added trifluoroacetic acid (8.00 mL, 104 mmol) and then heated at 80° C. After 16 h, additional ketone (3 eq) was added and heating continued. After a total of 3 days, the reaction mixture was basified (DCM-aq. NaHCO3) and the resulting precipitate was filtered, rinsed with DCM and dried to give an off-white solid. mp 302-304° C. dec.; MS m/z 473 [M+H]+.

Workup

temperatureheating
customAfter a total of 3 days
filtrationthe resulting precipitate was filtered
washrinsed with DCM
customdried
customto give an off-white solid

Sources & evidence

ORD record: ord-a434a5bf7d24493f9fae752eabd8a934
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765779B2

Reaction notes

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