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Potassium Carbonate → Methyl 2-(3-acetyl-5-(benzyloxy)-1H-indazol-1-yl)acetate

HRID 1527282
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HRID 1527282 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[C:18](=[O:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30]>CC#N>[C:18]([C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[N:14]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[N:13]=1)(=[O:20])[CH3:19]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 682835491-(5-(benzyloxy)-1H-indazol-3-yl)ethanone

생성물 1

HCID 68284049Methyl 2-(3-acetyl-5-(benzyloxy)-1H-indazol-1-yl)acetate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
90 °C

실험 절차

To 1-(5-(benzyloxy)-1H-indazol-3-yl)ethanone (3.50 g, 13.1 mmol) in CH3CN (100 mL) was added K2CO3 (4.54 g, 32.9 mmol) and methyl 2-bromoacetate (1.33 mL, 14.5 mmol). The reaction mixture was stirred at 90° C. for 90 min. The reaction mixture was filtered and the solid was washed with CH3CN. Volatiles were evaporated and then the crude mixture was purified by flash column chromatography on silica gel (gradient: c-hexane/EtOAc 1:1 to 1:3). TLC, Rf (c-hexane/EtOAc 1:3)=0.64; MS (LC/MS): 339.0 [M+H]+, 361.0 [M+Na]+; tR (HPLC conditions c): 5.09 min.

후처리

  1. filtrationThe reaction mixture was filtered
  2. washthe solid was washed with CH3CN
  3. customVolatiles were evaporated
  4. customthe crude mixture was purified by flash column chromatography on silica gel (gradient: c-hexane/EtOAc 1:1 to 1:3)
  5. custom5.09 min.

출처 및 근거

ORD 기록
ord-dff279ec04dc41e2bbe01914f212ffce
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09085555B2

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