Cesium carbonate → HCID 68596094, 화합물

HRID 1496643노트

반응식

HRID 1496643 반응식
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]

참가 물질

9

반응물 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 68595216methyl N-(5-bromo-2-chloro-anilino)carbamate2회

생성물 1

HCID 68596094HCID 68596094, 화합물

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 887Methanol용매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cc598027dc2d4899a7f5e2d321b3fa32
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09198433B2

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