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Hydrochloric Acid → Ethyl 3-[1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl]-4,4,4-trifluorobutanoat

HRID 1451527
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HRID 1451527 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[CH:13]([C:20]([F:23])([F:22])[F:21])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Br:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Br)=[CH:37][CH:36]=1.Cl>C1COCC1>[Br:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39][N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:6]([CH:13]([C:20]([F:23])([F:22])[F:21])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:7]2[CH3:12])=[CH:37][CH:36]=1
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HCID 313Hydrochloric AcidHCID 685274-Bromobenzyl bromideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 19974941Ethyl 3-(5-methoxy-2-methylindol-3-yl)-4,4,4-trifluorobutanoate

생성물 1

HCID 19974932Ethyl 3-[1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl]-4,4,4-trifluorobutanoat수율 64%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a -78° C. solution of the indole from Step 3 (3.1 g, 9.4 mmol) in 65 mL of THF was added KHMDS (0.6M toluene solution, 18.8 mL, 11.3 mmol) dropwise. The solution was warmed to 0° C., then cooled to -78° C. A solution of p-bromobenzyl bromide (3.0 g, 12.2 mmol) was then added, and the solution was allowed to warm to room temperature. The solution was then poured into 1M HCl and extracted with ether. The organic extracts were washed with brine, dried over MgSO4 and evaporated. The residue was purified by flash chromatography (20% ethyl acetate/hexanes) to provide 3.0 g of the title compound.

후처리

  1. temperaturecooled to -78° C
  2. temperatureto warm to room temperature
  3. extractionextracted with ether
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography (20% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-ea5fb29cbd5944c0a7f547a1785b3b58
출처 데이터셋
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05604253

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