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Cesium carbonate → HCID 136413571, 화합물

HRID 1050777
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HRID 1050777 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:28])=[C:8]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[N:19][S:18][C:9]2=[C:10]([C:12]#[C:13][Si](C)(C)C)[N:11]=1)=[O:5])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+]>CCO.C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([OH:28])=[C:8]2[C:20]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)=[N:19][S:18][C:9]2=[C:10]([C:12]#[CH:13])[N:11]=1)=[O:5])[CH3:2]
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참가 물질

4

반응물 2

HCID 10796Cesium carbonateHCID 136344026HCID 136344026, 화합물

생성물 1

HCID 136413571HCID 136413571, 화합물수율 56%

시약·촉매·용매 1

HCID 21584144Dichloromethane ethanol용매

실험 절차

To a solution of 3-(4-chloro-phenyl)-4-hydroxy-7-trimethylsilanylethynyl-isothiazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (0.189 mmol) in EtOH/CH2Cl2 (1/1, 0.76 mL) was added Cs2CO3 (0.227 mmol) with stirring at r.t. After 16 h the mixture was partitioned between 1N HCl (10 mL) and EtOAc (10 mL). The aqueous phase was extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine and water, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 0-20% EtOAc/CH2Cl2, to give the title compound (38 mg) as a white solid: MS (m/z) 357.0 (M−1).

후처리

  1. customAfter 16 h the mixture was partitioned between 1N HCl (10 mL) and EtOAc (10 mL)
  2. extractionThe aqueous phase was extracted with EtOAc (2×10 mL)
  3. washThe combined organic layers were washed with brine and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with 0-20% EtOAc/CH2Cl2

출처 및 근거

ORD 기록
ord-cef641c5513349c08b2bafe0b56725bc
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09387200B2

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