2-Chloromethyl-imidazo(1,2-A)pyridine → 2-(imidazo[1,2-a]pyridin-2-ylmethyl)-1H-isoindole-1,3(2H)-dione

HRID 1048699Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[CH:11]=1.[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.[K]>CN(C)C=O>[N:4]1[C:3]([CH2:2][N:16]2[C:12](=[O:22])[C:13]3[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:15]2=[O:17])=[CH:11][N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=12

Participants

Conditions

Temperature: 60 °C

Procedure

1.5 g (9 mmol) of 2-(chloromethyl)imidazo[1,2-a]pyridine were solubilised in 55 ml of dimethylformamide with magnetic stirring, 1.834 g (9.9 mmol) of potassium phthalimide were added portion wise and then the mixture was stirred at 60° C. for 2 h. The obtained solid was isolated by filtration, washed with 30 ml of diisopropyl ether and dried in a vacuum bell jar in order to obtain 1.81 g (yield=67%) of 2-(imidazo[1,2-a]pyridin-2-ylmethyl)isoindoline-1,3-dione as a white solid. LC-MS: m/z=278 (MH+); UV purity at 254 nm=93%. 1H NMR (300 MHz, DMSO) δ 8.45 (d, J=6.8 Hz, 1H), 7.96-7.67 (m, 5H), 7.45 (dd, J=9.1, 0.5 Hz, 1H), 7.33-7.14 (m, 1H), 6.84 (td, J=6.8, 1.1 Hz, 1H), 4.88 (s, 2H).

Workup

additionwere added portion wise
customThe obtained solid was isolated by filtration
washwashed with 30 ml of diisopropyl ether
customdried in a vacuum bell jar in order

Sources & evidence

ORD record: ord-afbf1679a3b44f5e9f4744a66efd1f85
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09381191B2

Reaction notes

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