Cesium carbonate → 3-(2-Phenoxyphenylamino)phthalic acid dimethyl ester

HRID 448355

반응식

HRID 448355 반응식
[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].[O:16]([C:23]1[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=1[NH2:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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:25][C:24]2[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=2[O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 75899Benzenamine, 2-phenoxy-HCID 634876Binap, (A+-)-HCID 2326127Dimethyl 3-iodophthalate

생성물 1

HCID 583072633-(2-Phenoxyphenylamino)phthalic acid dimethyl ester수율 73%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 3-iodophthalic acid dimethyl ester (1.0 g, 3.1 mmol), 2-phenoxyaniline (0.57 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 0.86 g of the product at 80:20 hexanes-ethyl acetate, in 73% yield: 1H NMR (CDCl3) δ 3.75 (s, 3H), 3.86 (s, 3H), 6.93-7.03 (m, 4H), 7.06-7.12 (m, 2H), 7.17 (dd, J=7.3 Hz, J=1.0 Hz, 1H), 7.29-7.38 (m, 4H), 7.46 (d, J=8.4 Hz, 1H), 7.89 (s, 1H).

후처리

  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 0.86 g of the product at 80:20 hexanes-ethyl acetate

출처 및 근거

ORD 기록
ord-6473256ac8d046dcad2dccea91f9a60d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481568B2

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