Cesium carbonate → HCID 58307277, compound

HRID 448314Notes

Reaction equation

HRID 448314 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10](I)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[CH2:16]1[O:25][C:24]2[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=2[O:17]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([NH:21][C:20]2[CH:22]=[CH:23][C:24]3[O:25][CH2:16][O:17][C:18]=3[CH:19]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 843101,3-Benzodioxol-5-amineHCID 634876Binap, (A+-)-HCID 2326127Dimethyl 3-iodophthalate

Product 1

HCID 58307277HCID 58307277, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-iodophthalic acid dimethyl ester (1.0 g, 3.1 mmol), 3,4-methylenedioxyaniline (0.43 g, 3.1 mmol), Pd2(dba)3 (0.13 g, 0.14 mmol), rac-BINAP (0.058 g, 0.093 mmol), and cesium carbonate (1.4 g, 4.3 mmol), in 6 mL toluene was heated to reflux under nitrogen for 24 hours. The reaction mixture was cooled, diluted with CH2Cl2 (10 mL), and then filtered through Celite, and the filter was washed with additional CH2Cl2 (30 mL). The filtrate was evaporated, and the residue was chromatographed using a hexanes-ethyl acetate gradient, eluting 0.69 g of the product at 85:15 hexanes-ethyl acetate, in 67% yield: 1H NMR (CDCl3) δ 3.87 (s, 3H), 3.88 (s, 3H), 5.97 (s, 2H), 6.63 (dd, J=8.2 Hz, J=2.1 Hz, 1H), 6.70 (d, J=2.1 Hz, 1H), 6.78 (d, J=8.2 Hz, 1H), 6.98 (dd, J=7.3 Hz, J=1.1 Hz, 1H), 7.13 (dd, J=7.3 Hz, J=1.1 Hz, 1H), 7.25 (t, J=7.9 Hz, 1H), 8.06 (br, 1H).

Workup

  1. temperatureto reflux under nitrogen for 24 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through Celite
  4. washthe filter was washed with additional CH2Cl2 (30 mL)
  5. customThe filtrate was evaporated
  6. customthe residue was chromatographed
  7. washeluting 0.69 g of the product at 85:15 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-217ff264cbea4e98a4916c41e0c50cae
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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