Hydrazine hydrate (1:1) → 4-(2-(2-(1-Trityl-1H-imidazol-4-yl)phenoxy)ethyl)aniline

HRID 1023835ノート

反応式

HRID 1023835 の反応式
[C:1]([N:20]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[OH:31])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CC1C=CC(S(O[CH2:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([N:53]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:49][CH:48]=2)(=O)=O)=CC=1.O.NN>CN(C=O)C.O>[C:1]([N:20]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH2:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([NH2:53])=[CH:49][CH:48]=2)[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

7

反応物 4

HCID 24654Hydrazine hydrate (1:1)HCID 24758Sodium hydrideHCID 582940602-(1-trityl-1H-imidazol-4-yl)phenolHCID 866730154-(1,3-Dioxoisoindolin-2-yl)phenethyl 4-methylbenzenesulfonate

生成物 1

HCID 672072114-(2-(2-(1-Trityl-1H-imidazol-4-yl)phenoxy)ethyl)aniline収率 60.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of the 2-(1-trityl-1H-imidazol-4-yl)phenol (1.1 g, 2.73 mmol) in DMF (15 mL) was added NaH (83 mg, 3.28 mmol) at 0° C. and the mixture was stirred at room temperature for 1 h. 4-(1,3-dioxoisoindolin-2-yl)phenethyl 4-methylbenzenesulfonate (1.15 g, 2.73 mmol) was added to the mixture. After stirring overnight under a nitrogen atmosphere, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with water (2×20 mL), brine (20 mL) and dried. The solvent was removed under reduced pressure and, the crude product was dissolved in ethanol (15 mL) and treated with hydrazine hydrate (0.3 mL, 5.46 mmol). The mixture was heated at 80° C. for 2 h and filtered. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography (silica gel, 30%-50% EtOAc/hexanes as eluent) to afford the desired product as a yellow solid (862 mg, 60% over two steps). 1H NMR: 2.63 (t, 2H, J=7.6 Hz), 4.03 (t, 2H, J=7.6 Hz), 6.46 (d, 1H, J=8.4 Hz), 6.80 (dd, 2H, J=12.4 Hz, 8 Hz), 6.99 (t, 1H, J=7.6 Hz), 7.10-7.19 (m, 7H), 7.28-7.31 (m, 9H), 7.41 (s, 1H), 7.52 (s, 1H), 8.18-8.21 (m, 1H), 8.63 (s, 1H), 9.11 (s, 1H).

後処理

  1. stirringAfter stirring overnight under a nitrogen atmosphere
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. washThe combined organic layers were washed with water (2×20 mL), brine (20 mL)
  4. customdried
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe crude product was dissolved in ethanol (15 mL)
  7. temperatureThe mixture was heated at 80° C. for 2 h
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was purified by flash column chromatography (silica gel, 30%-50% EtOAc/hexanes as eluent)

出典と根拠

ORDレコード
ord-5655af15940f4f659ed29358607853d9
出典データセット
uspto-grants-2014_05
特許番号
US08722720B2

反応ノート

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