Cesium carbonate → 5-Chloro-6-methoxy-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

HRID 225529Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12](I)=[C:13]([Cl:17])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19](=O)([O-])[O-:20].[Cs+].[Cs+]>CO.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:20][CH3:19])=[C:13]([Cl:17])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 140 °C

Procedure

Lit. Org. Lett. 2002, 4(6), 973-976. To a stirred suspension of 1.84 mmol 5-chloro-6-iodo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (Example A3(c)) in 7 ml methanol were added 0.18 mmol copper(I) iodide, 3.69 mmol cesium carbonate and 0.37 mmol 1,20-phenanthroline and the reaction mixture was stirred at 140° C. for 16 h. The mixture was then cooled to room temperature and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a light red solid. MS (m/e): 230.2 ({37Cl}[M+H− Me2C═CH2]+, 42%), 228.2 ({35Cl}[M+H− Me2C═CH2]+, 100%).

Workup

temperatureThe mixture was then cooled to room temperature
concentrationconcentrated in vacuo
customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Sources & evidence

ORD record: ord-358610146461498a8a3158bcb57f6c9d
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557114B2

Reaction notes

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