Diisopropylethylamine → HCID 24757386, compound

HRID 1640007Notes

Reaction equation

HRID 1640007 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][CH:3]=1.Br[CH2:18][C:19]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:20]=1[C:21](OCC)=[O:22].C(N(CC)C(C)C)(C)C>C(O)C>[Cl:30][C:27]1[CH:26]=[C:20]2[C:19]([CH2:18][N:1]([C:2]3[CH:3]=[CH:4][C:5]([CH:8]([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:6][CH:7]=3)[C:21]2=[O:22])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 13272463Ethyl 2-(bromomethyl)-5-chlorobenzoateHCID 22105824HCID 22105824, compound

Product 1

HCID 24757386HCID 24757386, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl 2-(4-aminophenyl)propanoate (0.24 g, 1.08 mmol), ethyl 2-(bromomethyl)-5-chlorobenzoate (0.25 g, 0.901 mmol) and N,N-diisopropylethylamine (0.14 g, 1.08 mmol) in ethanol (5 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-chloro-1-oxoisoindolin-2-yl)phenyl)propanoate (0.18 g, 55%) as a white solid: mp 169-171° C.; 1H NMR (500 MHz, CDCl3) δ 7.89 (d, J=2.5 Hz, 1H), 7.79 (d, J=8.5 Hz, 2H), 7.56 (dd, J=8.0, 2.0 Hz, 1H), 7.45 (d, J =8.0 Hz, 1H), 7.36 (d, J=8.5 Hz, 2H), 4.84 (s, 2H), 3.63 (m, 1H), 1.45 (d, J=7.5 Hz, 3H), 1.41 (s, 9H); ESI MS m/z 404 [M+H+CH3OH]+.

Workup

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

Sources & evidence

ORD record
ord-dac3f814c9434c969c813ddaba8da1e6
Source dataset
uspto-grants-2012_02
Patent number
US08110681B2

Reaction notes

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