Ethylenediaminetetraacetic Acid → Ethyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate

HRID 656029노트

반응식

HRID 656029 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:16]1[CH2:21][CH2:20][CH2:19]S[CH2:17]1.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.O[O:43][S:44]([O-:46])=O.[K+].C(=O)(O)[O-].[Na+]>COCCOC.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:16]1[CH2:21][CH2:20][CH2:19][S:44](=[O:46])(=[O:43])[CH2:17]1

참가 물질

7

반응물 4

HCID 6049Ethylenediaminetetraacetic AcidHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 59332762Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate

생성물 1

HCID 59332690Ethyl 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate수율 71%

시약·촉매·용매 2

HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

실험 절차

Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-3-yl)-1H-indole-7-carboxylate (0.375 g, 1.02 mmol) was dissolved in 1,2-Dimethoxyethane (DME) (25 mL). A solution of 0.0004M EDTA (7 mL) was added followed by the portion-wise addition of a suspension of oxone (1.88 g, 3.05 mmol) and sodium bicarbonate (0.855 g, 10.18 mmol) in 7 mL water. The reaction was stirred for 3 hours at room temperature. The reaction was diluted with water and extracted with dichloromethane. The combined organics were washed with water 2×. The combined aqueous layers were backwashed with dichloromethane. The combined organics were washed with water, brine, dried with MgSO4 and concentrated. The crude compound was purified by Combiflash silica column chromatography using 0-10% ethylacetate/dichloromethane on silica to give 0.290 g (71%) of the title compound.

후처리

  1. extractionextracted with dichloromethane
  2. washThe combined organics were washed with water 2×
  3. washThe combined organics were washed with water, brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe crude compound was purified by Combiflash silica column chromatography

출처 및 근거

ORD 기록
ord-ef1a9e66354b4369a79b3716d2fb0846
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071584B2

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