Cesium carbonate → HCID 68596094、化合物

HRID 1496643ノート

反応式

HRID 1496643 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:14])=[C:6]([NH:8][NH:9][C:10]([O:12][CH3:13])=[O:11])[CH:7]=1.[F:15][C:16]([F:28])([F:27])[O:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.CO.C(OCC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:14][C:5]1[CH:4]=[CH:3][C:2]([C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([O:17][C:16]([F:15])([F:27])[F:28])[CH:19]=2)=[CH:7][C:6]=1[NH:8][NH:9][C:10]([O:12][CH3:13])=[O:11]

参加物

9

反応物 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 68595216methyl N-(5-bromo-2-chloro-anilino)carbamate2 回

生成物 1

HCID 68596094HCID 68596094、化合物

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

A mixture of methyl 2-(5-bromo-2-chlorophenyl)hydrazine carboxylate (i.e. the product of Step B) (1.27 g, 4.5 mmol), [3-(trifluoromethoxy)phenyl]boronic acid (1.85 g, 9 mmol), cesium carbonate (2.9 g, 9 mmol), tris(dibenzylideneacetone)dipalladium (0.18 g, 0.2 mmol) and triphenylphosphine (1.2 g, 4.5 mmol) in toluene (60 mL) and methanol (60 mL) was heated at refluxed for 24 h. After cooling, the reaction mixture was taken up in diethyl ether and washed with water. After drying over sodium sulfate, the solvent was removed under reduced pressure. The residue was purified by flash chromatography using 25% ethyl acetate in hexanes as eluant to afford a solid matieral (1.3 g), which was a mixture of starting material and the title compound.

後処理

  1. temperaturewas heated
  2. temperatureat refluxed for 24 h
  3. temperatureAfter cooling
  4. washwashed with water
  5. dry with materialAfter drying over sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by flash chromatography
  8. customto afford a solid matieral (1.3 g), which
  9. additiona mixture of starting material

出典と根拠

ORDレコード
ord-cc598027dc2d4899a7f5e2d321b3fa32
出典データセット
uspto-grants-2015_12
特許番号
US09198433B2

反応ノート

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