Isoindoline → Tert-butyl {2-[2-(1,3-dihydroisoindol-2-yl)-2-oxoacetyl]-4-iodophenyl}carbamate

HRID 1631100Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6](=[O:18])[C:5]2=[O:19].[CH2:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][NH:21]1>C1COCC1>[CH2:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][N:21]1[C:6](=[O:18])[C:5]([C:4]1[CH:3]=[C:2]([I:1])[CH:10]=[CH:9][C:8]=1[NH:7][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:19]

Participants

Conditions

Temperature: 25 °C

Procedure

62.41 g of tert-butyl 5-iodo-2,3-dioxo-2,3-dihydroindole-1-carboxylate are dissolved in dried THF, and 18.98 ml of 2,3-dihydro-1H-isoindole are added. The mixture is stirred at 25° C. for 30 min, evaporated to dryness in vacuo, and the residue is triturated with petroleum ether, filtration gives 82.3 g of tert-butyl {2-[2-(1,3-dihydroisoindol-2-yl)-2-oxoacetyl]-4-iodophenyl}carbamate (beige solid); LC-MS retention time: 2.63 min;

Workup

customevaporated to dryness in vacuo
filtrationthe residue is triturated with petroleum ether, filtration

Sources & evidence

ORD record: ord-a88d96af3477485f858b615689dc5a0e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791129B2

Reaction notes

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