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Water → 3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazol-6-ylamine

HRID 724380
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HRID 724380 반응식
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH:21]=[CH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:9][N:10]2[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])=[CH:6][CH:5]=1)([O-])=O.Cl[Sn]Cl.O.[OH-].[Na+]>CN(C=O)C.CCOC(C)=O>[CH:21]([C:8]1[C:7]2[C:11](=[CH:12][C:4]([NH2:1])=[CH:5][CH:6]=2)[N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:19])([CH3:18])[CH3:20])[N:9]=1)=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 693543436-nitro-3-styryl-1-[2-(trimethyl-silanyl) ethoxymethyl]-1H-indazole

생성물 1

HCID 693709803-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazol-6-ylamine수율 68.1%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

6-Nitro-3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazole (8.1 g, 20.5 mmol) was dissolved in DMF (75 mL) at 23° C. under an atmosphere of argon. SnCl2 (12.9 g, 67.7 mmol) was added followed by water (1.7 mL, 92.2 mmol) and the resulting mixture was heated to 50° C. After 4 h, 3N NaOH (45 mL, 135 mmol) was added followed by EtOAc (100 mL). The resulting emulsion was filtered hot through Celite and the bed of Celite was washed with hot EtOAc (3×100 mL). The filtrate was concentrated under reduced pressure, the residue was dissolved in EtOAc, washed with brine, dried with Na2SO4, filtered and concentrated under reduced pressure to give a solid. The crude material was purified by silica gel chromatography (2:8→7:3 ethyl acetate:hexane), to give 3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazol-6-ylamine as a yellow solid (5.1 g, 68% yield). MS (FAB) [M+H]/z Calc'd 366. found 366.

후처리

  1. filtrationThe resulting emulsion was filtered hot through Celite
  2. washthe bed of Celite was washed with hot EtOAc (3×100 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with brine
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a solid
  10. customThe crude material was purified by silica gel chromatography (2:8→7:3 ethyl acetate:hexane)

출처 및 근거

ORD 기록
ord-5ca2550217d54ad6b850e158bff79655
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07141587B2

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