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Cesium carbonate → 3-[4-(2-Dimethylamino-ethoxy)-2-isopropoxy-phenylamino]-phthalic acid dimethyl ester

HRID 448382
Notes
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Reaction equation

HRID 448382 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].[CH3:16][N:17]([CH3:32])[CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[C:23]([O:28][CH:29]([CH3:31])[CH3:30])[CH:22]=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:27][C:24]2[CH:25]=[CH:26][C:21]([O:20][CH2:19][CH2:18][N:17]([CH3:32])[CH3:16])=[CH:22][C:23]=2[O:28][CH:29]([CH3:31])[CH3:30])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2326127Dimethyl 3-iodophthalateHCID 583071884-(2-Dimethylaminoethoxy)-2-isopropoxyphenylamine

Product 1

HCID 583073113-[4-(2-Dimethylamino-ethoxy)-2-isopropoxy-phenylamino]-phthalic acid dimethyl esterYield 47%

Reagents, catalysts & solvents

3
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-iodophthalic acid dimethyl ester (2.0 g, 6.2 mmol), 4-(2-dimethylaminoethoxy)-2-isopropoxyphenylamine (1.5 g, 6.2 mmol), Pd2(dba)3 (0.26 g, 0.28 mmol), rac-BINAP (0.12 g, 0.19 mmol), and cesium carbonate (2.8 g, 8.6 mmol), in 12 mL toluene was heated to reflux under nitrogen for 24 hours. The reaction mixture was cooled, diluted with CH2Cl2 (20 mL), and filtered through Celite, and the filter was washed with additional CH2Cl2 (60 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 1.3 g of the product at 96:4 methylene chloride-methanol, in 47% yield; 1H NMR (CDCl3) δ 1.31 (d, J=6.1 Hz, 6H), 2.96 (d, J=4.8 Hz, 6H), 3.41-3.47 (m, 2H), 3.87 (s, 6H), 4.47-4.51 (m, 3H), 6.45 (dd, J=8.7 Hz, J=2.6 Hz, 1H), 6.56 (d, J=2.6 Hz, 1H), 7.07 (dd, J=6.0 Hz, J=2.5 Hz, 1H), 7.18 (d, J=8.7 Hz, 1H), 7.20-7.18 (m, 2H), 7.90 (s, 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 (60 mL)
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by ISCO silica gel flash chromatography
  7. washeluting 1.3 g of the product at 96:4 methylene chloride-methanol

Sources & evidence

ORD record
ord-f0485f090fdb41a5b6e4126d0d0ae622
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08481568B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes