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

HRID 387269ノート

反応式

HRID 387269 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7a17fb518e074e54b7bfad8395efb3af
出典データセット
uspto-grants-2013_02
特許番号
US08372875B2

反応ノート

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