3-{[(2-Iodo-phenyl)-(3-phenyl-propynoyl)-amino]-methyl}-benzoic acid methyl ester → 3-{3-[4-methyl-1-phenyl-pent-(Z)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester

HRID 1623473노트

반응식

HRID 1623473 반응식
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2I)[C:12](=[O:21])[C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]=1.[Br-].[CH3:31][CH:32]([CH3:36])[CH2:33][CH2:34][Zn+]>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)/[C:13](=[C:14](/[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)\[CH2:34][CH2:33][CH:32]([CH3:36])[CH3:31])/[C:12]2=[O:21])[CH:5]=1

참가 물질

5

반응물 2

HCID 670363063-{[(2-Iodo-phenyl)-(3-phenyl-propynoyl)-amino]-methyl}-benzoic acid methyl esterHCID 178445882HCID 178445882, 화합물

생성물 1

HCID 510344403-{3-[4-methyl-1-phenyl-pent-(Z)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester수율 28%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

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온도
40 °C

실험 절차

To a degassed refluxing solution of 3-{[(2-iodo-phenyl)-(3-phenyl-propynoyl)-amino]-methyl}-benzoic acid methyl ester (100 mg, 0.2 mmol) and Ni(PPh3)2I2 (16 mg, 0.02 mmol) in CH2Cl2 (8 ml) was added 3-methylbutylzinc bromide (151 mg, 0.7 mmol) in CH2Cl2 (1 ml). The reaction was stirred at 40° C. for 6 h and then the solution was cooled to room temperature. The resultant solution was diluted with ethyl acetate (50 ml). The organic layer was washed with aqueous HCl solution (4%, 10 ml), brine (3×10 ml). The aqueous layer was back-extracted with ethyl acetate (3×10 ml). The combined organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel, eluting with petrol ether-ethyl acetate, to give 3-{3-[4-methyl-1-phenyl-pent-(Z)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester (24 mg, 28%) as light yellow solid. 1H NMR (300 Hz, CDCl3): δppm 0.88 (d, 6H), 1.43-1.55 (m, 2H), 1.68-1.72 (m, 1H), 2.93-2.99 (m, 2H), 3.91 (s, 3H), 4.89 (s, 2H), 6.64 (d, 1H), 7.05 (t, 1H), 7.15 (t, 1H), 7.28-7.38 (m, 4H), 7.40-7.47 (m, 3H), 7.62 (d, 1H), 7.91 (d, 1H), 7.95 (s, 1H); and 3-{3-[4-methyl-1-phenyl-pent-(E)-ylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester (29 mg, 33%) as light yellow solid. 1H NMR (300 Hz, CDCl3): δ ppm 0.88 (d, 6H), 1.36-1.44 (m, 2H), 1.64-1.68 (m, 1H), 3.33-3.38 (m, 2H), 3.91 (s, 3H), 5.04 (s, 2H), 6.01 (d, 1H), 6.58-6.61 (m, 2H), 6.96-7.02 (t, 1H), 7.26-7.29 (m, 2H), 7.37 (t, 2H), 7.43-7.52 (m, 3H), 7.93 (d, 1H), 8.03 (s, 1H).

후처리

  1. temperaturethe solution was cooled to room temperature
  2. washThe organic layer was washed with aqueous HCl solution (4%, 10 ml), brine (3×10 ml)
  3. extractionThe aqueous layer was back-extracted with ethyl acetate (3×10 ml)
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel
  8. washeluting with petrol ether-ethyl acetate

출처 및 근거

ORD 기록
ord-da3ef55dd16a452aa03b7050c04dbe93
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778973B2

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