Diisopropylethylamine → HCID 57429425, compound

HRID 1640013Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:13]Br)=[C:6]([CH:12]=1)[C:7]([O:9]CC)=O.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:30])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:18][CH:17]=1.C(N(CC)C(C)C)(C)C>C(O)C>[Br:1][C:2]1[CH:12]=[C:6]2[C:5]([CH2:13][N:15]([C:16]3[CH:17]=[CH:18][C:19]([CH:22]([CH3:30])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:20][CH:21]=3)[C:7]2=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of ethyl 5-bromo-2-(bromomethyl)benzoate (4.00 g, 12.4 mmol), tert-butyl 2-(4-aminophenyl)propanoate (3.4 g, 15.4 mmol) and N,N-diisopropylethylamine (1.98 g, 15.4 mmol) in ethanol (120 mL) was heated in a sealed tube at 100° C. overnight. After this time, the mixture was cooled with an ice bath and the solids collected by filtration to afford tert-butyl 2-(4-(6-bromo-1-oxoisoindolin-2-yl)phenyl)propanoate (2.00 g, 39%) as a white solid: mp 164-165° C.: 1H NMR (300 MHz, CDCl3) δ 8.06 (d, J=1.7 Hz, 1H), 7.81-7.77 (m, 2H), 7.71 (dd, J=8.0, 1.8 Hz, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.38-7.34 (m, 2H), 4.81 (s, 2H), 3.63 (q, J=7.1 Hz, 1H), 1.46 (d, J=7.2 Hz, 3H), 1.41 (s, 9H); ESI MS m/z 448 [M+H+CH3OH]+.

Workup

temperatureAfter this time, the mixture was cooled with an ice bath
filtrationthe solids collected by filtration

Sources & evidence

ORD record: ord-2036c5471e394a159a51e0d31d10c317
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110681B2

Reaction notes

Loading…