Cesium carbonate → HCID 58307173, compound

HRID 448378Notes

Reaction equation

HRID 448378 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.[CH3:14][O:15][C:16](=[O:28])[C:17]1[C:18](=[C:23](I)[CH:24]=[CH:25][CH:26]=1)[C:19]([O:21][CH3:22])=[O:20].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]>[CH3:22][O:21][C:19](=[O:20])[C:18]1[C:17](=[C:26]([NH:12][C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:13])[CH3:1])=[CH:7][CH:8]=2)[CH:25]=[CH:24][CH:23]=1)[C:16]([O:15][CH3:14])=[O:28]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2326127Dimethyl 3-iodophthalateHCID 64846554-[2-(Dimethylamino)ethoxy]aniline

Product 1

HCID 58307173HCID 58307173, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2-dimethylamino-ethoxy)-phenylamine (0.56 g, 3.1 mmol), 3-iodophthalic acid dimethyl ester (1.0 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 16 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 in vacuo, and the residue was purified by ISCO silica gel flash chromatography using a methylene chloride-methanol gradient, eluting 0.53 g of the product at 95:5 methylene chloride-methanol, in 46% yield, as a pale yellow solid; 1H NMR (CDCl3) δ 2.34 (s, 3H), 2.73 (t, J=5.7 Hz, 2H), 3.86 (s, 3H), 3.88 (s, 3H), 4.06 (t, J=5.7 Hz, 2H), 6.89-6.96 (m, 3H), 7.06-7.23 (m, 3H), 7.33-7.50 (m, 1H), 8.09 (s, 1H).

Workup

  1. temperatureto reflux under nitrogen for 16 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 in vacuo
  6. customthe residue was purified by ISCO silica gel flash chromatography
  7. washeluting 0.53 g of the product at 95:5 methylene chloride-methanol

Sources & evidence

ORD record
ord-a372c3dabfce424abe73cefe7c5309c1
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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