Triethylamine → N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)phenyl)acetamide

HRID 1754112노트

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HRID 1754112 반응식
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Na+].[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.CCN(CC)CC.[NH4+].[OH-]>O1CCOCC1.CS(C)=O.[Cl-].[Na+].O.CC([O-])=O.CC([O-])=O.[Cu+2].CCOC(C)=O>[F:15][C:16]([F:27])([F:28])[O:17][C:18]1[CH:23]=[C:22]([S:11]([C:8]2[CH:7]=[CH:6][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:10][CH:9]=2)(=[O:13])=[O:12])[CH:21]=[CH:20][CH:19]=1

참가 물질

10

반응물 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 23666794Sodium 4-acetamidobenzene-1-sulfinate

생성물 1

HCID 70978998N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)phenyl)acetamide수율 57.9%

시약·촉매·용매 5

HCID 8895Cupric acetate촉매HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매HCID 57417360Sodium chloride; water용매

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온도
60 °C

실험 절차

To a solution of sodium 4-acetamidobenzenesulfinate dehydrate (128 mg, 0.5 mmol), 3-trifluoromethoxy-phenylboronic acid (144 mg, 0.75 mmol) and Et3N (0.313 mL, 2.25 mmol) in 1,4-dioxane (4 mL) and DMSO (4 mL) is added Cu(OAc)2 (114 mg, 0.625 mmol). The mixture is heated at 60° C. for 16 h then cooled to ambient temperature. EtOAc (12 ml) and brine (6 ml) is added followed by concentrated NH4OH (0.6 mL) and the mixture is stirred at ambient temperature for 15 min. The layers are separated and the aqueous layer is extracted with EtOAc (6 mL). The combined extracts are dried (Na2SO4) and evaporated. The residue is purified by preparative TLC with 2:1 EtOAc/hexanes to give 104 mg (57%) white solid.

후처리

  1. temperaturethen cooled to ambient temperature
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with EtOAc (6 mL)
  4. dry with materialThe combined extracts are dried (Na2SO4)
  5. customevaporated
  6. customThe residue is purified by preparative TLC with 2:1 EtOAc/hexanes

출처 및 근거

ORD 기록
ord-8008021cc14c4081b4213b819b0bdec4
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169209B2

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