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

HRID 1754112ノート

反応式

HRID 1754112 の反応式
[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

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 8895Cupric acetate触媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8008021cc14c4081b4213b819b0bdec4
出典データセット
uspto-grants-2015_10
特許番号
US09169209B2

反応ノート

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