2-Chloromethyl 2-(trimethylsilyl)ethyl ether → 3-Chloro-5-(1,3-dioxan-2-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

HRID 1038399노트

반응식

HRID 1038399 반응식
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]3[O:16][CH2:15][CH2:14][CH2:13][O:12]3)[CH:9]=2)[NH:4][N:3]=1.CC(C)([O-])C.[Na+].[CH3:23][Si:24]([CH3:31])([CH3:30])[CH2:25][CH2:26][O:27][CH2:28]Cl>C1COCC1>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:11]3[O:16][CH2:15][CH2:14][CH2:13][O:12]3)[CH:9]=2)[N:4]([CH2:28][O:27][CH2:26][CH2:25][Si:24]([CH3:31])([CH3:30])[CH3:23])[N:3]=1

참가 물질

5

반응물 3

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 23676156Sodium t-butoxideHCID 1784784203-Chloro-5-(1,3-dioxan-2-yl)-1H-indazole

생성물 1

HCID 584075883-Chloro-5-(1,3-dioxan-2-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-indazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 2.7 g (11.3 mmol) 3-chloro-5-(1,3-dioxan-2-yl)-1H-indazole (Example 44A) in anhydrous THF (60 ml) were added 1.31 g (13.6 mmol) sodium tert-butoxide at room temperature. The solution was cooled to 0° C., and 2.26 g (13.6 mmol) 2-(trimethylsilyl)ethoxymethyl chloride were added at this temperature. The resulting mixture was stirred at 0° C. for 1 h and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water and with brine. The organic layer was dried with sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography (silica gel; cyclohexane/ethyl acetate 5:1 v/v) to give 1.73 g (41% of th.) of the title compound.

후처리

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water and with brine
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by flash chromatography (silica gel; cyclohexane/ethyl acetate 5:1 v/v)

출처 및 근거

ORD 기록
ord-a6d8d1eefdf74af5a4b1c6a65d6bc164
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551989B2

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