Dimethylformamide → 1-[5-(3-Chloro-5-nitrophenyl)-1,3-thiazol-2-yl]cyclobutanol

HRID 1039993노트

반응식

HRID 1039993 반응식
[Cl:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.CC(O)(C(C)(O)C)C.Br[C:29]1[S:33][C:32]([C:34]2([OH:38])[CH2:37][CH2:36][CH2:35]2)=[N:31][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:29]2[S:33][C:32]([C:34]3([OH:38])[CH2:37][CH2:36][CH2:35]3)=[N:31][CH:30]=2)[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 584562241-(5-Bromothiazol-2-yl)cyclobutanolHCID 674337372,3-Dimethylbutane-2,3-diol 2-(3-chloro-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 674321141-[5-(3-Chloro-5-nitrophenyl)-1,3-thiazol-2-yl]cyclobutanol수율 54.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

The product of Step 1 (1.6 g, 3.98 mmol), Intermediate 1 (839 mg, 3.58 mmol), PdCl2 (dppf)-dichloromethane adduct (163 mg, 0.199 mmol), sodium carbonate (2M in water) (5.97 mL, 11.95 mmol), and DMF (39.8 mL) were heated at 100° C. for 2 hours under nitrogen. The reaction mixture was diluted with ethyl acetate and water, the solids were filtered and the organic fraction was washed with water, brine and dried over Na2SO4. Filtration and solvent evaporation gave a residue which was further purified by column chromatography on silica gel, eluting with ethyl acetate/hexane with a gradient 30-50% to afford 1-[5-(3-chloro-5-nitrophenyl)-1,3-thiazol-2-yl]cyclobutanol (610 mg, 49.3%).

후처리

  1. filtrationthe solids were filtered
  2. washthe organic fraction was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and solvent evaporation
  5. customgave a residue which
  6. customwas further purified by column chromatography on silica gel
  7. washeluting with ethyl acetate/hexane with a gradient 30-50%

출처 및 근거

ORD 기록
ord-1607a593369245edba7db38d6ffc3d3e
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551984B2

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