Cesium carbonate → HCID 58307319, compound

HRID 448328Notes

Reaction equation

HRID 448328 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].[NH2:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[CH2:22][CH2:21][CH2:20]2.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:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[CH2:22][CH2:21][CH2:20]3)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 90496Indan-5-amineHCID 634876Binap, (A+-)-HCID 2326127Dimethyl 3-iodophthalate

Product 1

HCID 58307319HCID 58307319, compoundYield 82%

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), 5-aminoindan (0.42 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 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 0.82 g of the product at 85:15 hexanes-ethyl acetate, in 82% yield: 1H NMR (CDCl3) δ 2.09 (m, 2H), 2.88 (t, J=7.4 Hz, 4H), 3.86 (s, 3H), 3.88 (s, 3H), 6.93 (dd, J=7.9 Hz, J=1.8 Hz, 1H), 6.99-7.06 (m, 2H), 7.12-7.21 (m, 1H), 7.25-7.29 (m, 1H), 7.40-7.71 (m, 1H), 8.07 (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 0.82 g of the product at 85:15 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-eecda03b95144751abb561662227f1fa
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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