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

HRID 1039993ノート

反応式

HRID 1039993 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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%

出典と根拠

ORDレコード
ord-1607a593369245edba7db38d6ffc3d3e
出典データセット
uspto-grants-2013_10
特許番号
US08551984B2

反応ノート

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