Cesium carbonate → 4-(4-Ethoxycyclohex-1-enyl)-2-methyl-7-nitro-2,3-dihydro-isoindol-1-one

HRID 511391Notes

Reaction equation

O1CCOCC1.[CH2:7]([O:9][CH:10]1[CH2:15][CH2:14][C:13](OS(C(F)(F)F)(=O)=O)=[CH:12][CH2:11]1)[CH3:8].[CH3:24][N:25]1[CH2:33][C:32]2[C:27](=[C:28]([N+:43]([O-:45])=[O:44])[CH:29]=[CH:30][C:31]=2B2OC(C)(C)C(C)(C)O2)[C:26]1=[O:46].C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH2:7]([O:9][CH:10]1[CH2:15][CH2:14][C:13]([C:31]2[CH:30]=[CH:29][C:28]([N+:43]([O-:45])=[O:44])=[C:27]3[C:32]=2[CH2:33][N:25]([CH3:24])[C:26]3=[O:46])=[CH:12][CH2:11]1)[CH3:8]

Participants

Conditions

Temperature: 60 °C

Procedure

Dioxane (20 mL) and water (5 mL) were taken in a three necked RB flask equipped with a nitrogen inlet and a thermometer. The solvents were deoxygenated for 15 min using nitrogen gas. Trifluoro-methanesulfonic acid 4-ethoxy-cyclohex-1-enyl ester (Compound 166D, 300 mg, 1.1 mmol), 2-methyl-7-nitro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (Compound 205E, 630 mg, 1.64 mmol), tetrakis triphenyl phosphine palladium catalyst (114 mg, 0.01 mmol) and cesium carbonate (889 mg, 2.7 mmol) were added. The reaction mixture was heated to 60° C. for 3 hrs. The solvents were evaporated and the residue was purified over silica gel column using (methanol:methylene chloride: 1:99). Yield: 300 mg (86%). 1H NMR (CDCl3, 400 MHz): δ 1.2 (t, 3H, J=7 Hz), 1.8-2.4 (m, 6H), 3.15 (s, 3H), 3.50-3.64 (m, 3H), 4.36 (s, 2H), 5.79 (m, 1H), 7.4 (d, 1H, J=8.1 Hz), 7.63 (d, 1H, J=8.1 Hz).

Workup

customequipped with a nitrogen inlet
customThe solvents were deoxygenated for 15 min
customThe solvents were evaporated
customthe residue was purified over silica gel column

Sources & evidence

ORD record: ord-511e19a6b44b47c3a97af3e22ae4f51e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096624B2

Reaction notes

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